3-Amino-3-methyl-1-butanol

Step 3 2, 4, 4-Trimethyl-5, 6-dihydro-4H-[1, 3]oxazine (25.2 g, 0.20 mol) was dissolved in 6 N NaOH (65 mL, 0.40 mol) and stirred at 80 °C for 18 h. The resulting mixture was cooled to 25 °C and extracted with CHB 3-Amino-3-methyl-butan-1-ol 2, 4, 4-Trimethyl-5, 6-dihydro-4H-[1, 3]oxazine (25.2 g, 0.20 mol) was dissolved in 6 N NaOH (65 mL, 0.40 mol) and stirred at 80 C. for 18 h. The resulting mixture was cooled to 25 C. and extracted with CH2Cl2 (3*100 mL). The organic was dried (MgSO4) and concentrated to afford the desired material as a colorless oil (5.1 g, 20%): 1H NMR (DMSO-d6) delta 3.55 (t, 2H, J=7 Hz), 1.47 (t, 2H, J=7 Hz), 1.03 (s, 6H).Step 3: 3-Amino-3-methyl-butan-1-ol. 2, 4, 4-Trimethyl-5, 6-dihydro-4H-[1, 3]oxazine(25.15 g, 0.20 mol) was dissolved in 6N NaOH(65 mL, 0.40 mol) and stirred at 80 C. for 18 h. The resulting mixture was cooled to 25 C. and extracted with CH2Cl2(3*100 mL). The organic was dried(MgSO4) and concentrated to afford the desired material as a colorless oil(5.1 g, 20%); 1H NMR (DMSO-d6) delta 3.55 (t, J=7 Hz, 2H), delta 1.47 (t, J=7 Hz, 2H), delta 1.03 (s, 6H).2, 4, 4-Trimethyl-5, 6-dihydro-4H-[1, 3]oxazine (25.2 g, 0.20 mol) was dissolved in 6 N NaOH (65 mL, 0.40 mol) and stirred at 80 C for 18 h. The resulting mixture was cooled to 25 C and extracted with CH2Cl2 (3 x 100 mL). The organic was dried (MgSO4) and concentrated to afford the desired material as a colorless oil (5.1 g, 20%): 1H NMR (DMSO-d6) delta 3.55 (t, 2H, J = 7 Hz), 1.47 (t, 2H, J = 7 Hz), 1.03 (s, 6H).3-Amino-3-methyl-butan-1-ol (5.0 g, 0.04 mol) was dissolved in 150 mL CH2Cl2 and treated with di-tert-butyl dicarbonate (11.12 g, 0.05 mol). The resulting mixture was stirred for 18 h at 25 C. The mixture was concentrated to the desired material as an amber oil (9.8 g, 100%): 1H NMR (DMSO-d6) delta 3.55 (s, 1H), 4.43 (t, 1H, J = 5 Hz), 3.46 (m, 2H), 1.71 (t, 2H, J = 7 Hz), 1.37 (s, 9H), 1.12 (s, 6H).Step 1: tert-butyl (3-hydroxy-1, 1-dimethyl-propyl)-carbamate 88.2 g (404 mmol) di-tert.-butyldicarbonate are added batchwise at ambient temperature to a solution of 41.3 g (400 mmol) 3-amino-3-methyl-butanol in 250 mL ethyl acetate. The reaction mixture is stirred for 18 hours at RT and then concentrated by evaporation in the rotary evaporator. 81.3 g (400 mmol, quantitative) tert-butyl (3-amino-1, 1-dimethyl-propyl)-carbamate are obtained. Rf=0.48 [silica gel, petroleum ether/ethyl acetate (1/1)] MS [ESI (M+H)+]=204To a solution of b 3-(N-BOC-amino)-3-methyl-butan-1-ol A solution of 24.88 g (0.114 mol) of di-tert-butyl dicarbonate in 70 ml of methylene chloride is added dropwise to a solution of 11.2 g (0.1086 mol) of C (3-Hydroxy-1, 1-dimethyl-propyl)-carbamic Acid Tert-Butyl Ester 3-Amino-3-methyl-butan-1-ol (5.0 g, 0.04 mol) was dissolved in 150 mL CH2Cl2 and treated with di-tert-butyl dicarbonate (11.12 g, 0.05 mol). The resulting mixture was stirred for 18 h at 25 C. The mixture was concentrated to the desired material as an amber oil (9.8 g, 100%): 1H NMR (DMSO-d6) delta 3.55 (s, 1H), 4.43 (t, 1H, J=5 Hz), 3.46 (m, 2H), 1.71 (t, 2H, J=7 Hz), 1.37 (s, 9H), 1.12 (s, 6H).Step 4: (3-Hydroxy-1, 1-dimethyl-propyl)-carbamic acid tert-butyl ester. 3-Amino-3-methyl-butan-1-ol(5.0 g, 0.04 mol) was dissolved in 150 mL CH2Cl2 and treated with di-tert-butyl dicarbonate(11.12 g, 0.05 mol). The resulting mixture was stirred for 18 h at 25 C. The mixture was concentrated to the desired material as an amber oil(9.8 g, 100%); 1H NMR (DMSO-d6) delta 3.55 (s, 1H), delta 4.43 (t, J=5 Hz, 1H), delta 3.46 (m, 2H), delta 1.71 (t, J=7 Hz, 2H), delta 1.37(s, 9H), delta 1.12(s, 6H).a. Tert-butyl (3-hvdroxy-1 , 1-dimethylpropyl)-carbamidate200 g (1.94 mol) 3-amino-3-methylbutan-1 -ol in 0.75 I ethyl acetate are combined with a solution of 435.0 g (1.99 mol) di-tert-butyl-dicarbonate in 0.75 I ethyl acetate within one hour. The reaction mixture is stirred for 30 min and the solvent is eliminated in vacuo. The residue obtained is used in the next step without further purification. Yield: 412.5 g1H-NMR (DMSO, 400 MHz): 1.19 (s, 9H); 1.36 (s, 6H); 1.68-1.74 (m, 2H); 3.42-3.50 (m, 2H); 4.39 (t, J = 4.8, 1 H); 6.36 (br s, 1 H).Alternatively, tert-butyl (3-hydroxy-1 , 1-dimethylpropyl)-carbamidate may also be prepared by the methods described for example in J. of Labell. Compounds & Radioph. 2001 , 44(4), 265-275 or WO 03/037327, p. 82/83.Component XI [preparation of the compound of formula (IIIb)]N-tert-butoxycarbonyl-4, 4-dimethyl-[1, 2, 3]oxathiazinane-2, 2-dioxide a. tert-butyl (3-hydroxy-1, 1-dimethylpropyl)-carbamidate Intermediate X: 3, 3-dimethyl-1-oxo-2, 3, 4, 5-tetrahydro-1H-[1, 4]diazepino[1, 2- a]indole-8-carboxylic acid Step 1: Synthesis of tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate To a solution of To a solution of Synthesis of tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate Into a 200-mL round-bottom flask under a nitrogen atmosphere, was placed a solution of 3-amino-3- methylbutan-1 -ol (2.5 g, 24.2 mmol, 1 equiv) and TEA (4.9 g, 48.5 mmol, 2 equiv) in anhydrous DCM (50 ml_). The mixture was stirred for 10 minutes at 25C. Then (Boc)20 (5.3 g, 24.2 mmol, 1 equiv) was added in one portion. The resulting solution was stirred for 6 hours at 25 C. The reaction was then quenched by the addition of water (20 ml_). The resulting solution was extracted with dichloromethane (3x30 ml.) and the organic layers combined was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuum. This resulted in tert- butyl N-(4-hydroxy-2-methylbutan-2-yl)carbamate which was used in the next step directly.

Molecular Weight:103.16
XLogP3:-0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:103.099714038
Monoisotopic Mass:103.099714038
Topological Polar Surface Area:46.2
Heavy Atom Count:7
Complexity:52
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes