(1S,2S)-trans-2-Aminocyclopentanol hydrochloride

General procedure: Carboxylic acid (1 eq.) was dissolved in anhydrous dimethylformamide. Amine (1-2 eq.), N- ethyl-N-diisopropylamine (4 eq.) and propane phosphonic acid anhydride (T3P, 1.5 eq., 50% in DMF) were successively added. After stirring over night at rt the reaction mixture was purified directly by HPLC or quenched with water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous ammonium hydrochloride solution, dried over sodium sulfate, filtered and concentrated under vacuum to yield the crude title compound. In general the crude products were purified by RP-HPLC (methods A-D depending on polarity). It is also possible to apply the reaction mixture immediately to RP- HPLC.Trans-(1S, 2S)-2-Aminocyclopentanol hydrochloride 15-1(CAS: 68327-04-8) (1.37 g, 10 mmol) and Et3N (3 g, 30 mmol) were added to 40 mL of toluene and stirred at RT for 5 mins. Then phthalic anhydride (1.48 g, 10 mmol) wasadded under stirring and the reaction mixture was refluxed under stirring for 4 h. TLC showed the reaction was completed.After cooled to r. t., the reaction mixture was quenched with 40mL of water. The organic layer was dried with anhydrousNa2SO4 and concentrated under reduced pressure. The residue was purified with chromatography column to give 1.7g white solid, 73.5%.General procedure: A DMF solution (5 mL) containing HOBt (54 mg), EDCI (76.7 mg), and D7 (105 mg) was stirred at roomtemperature for 10 mins under N2. Morpholin-4-ylamine (49mg) (CAS: 4319-49-7) and DIPEA (130mg) were added tothe reaction mixture by turn. The mixture was stirred at RT for 60h. TLC (DCM: MeOH=20:1, Rf=0.3) showed the startingmaterial was consumed completely.To the reaction mixture were added DCM (25 mL) and 30 mL water. The organiclayer was washed with water (20mL*2), dried over anhydrous Na2SO4, and concentrated under reduced pressure. Theresidue was purified by silica gel column to give product Da (76.4 mg, 65%) as white solid.General procedure: A DMF solution (5 mL) containing HOBt (68 mg, 0.496 mmol), EDCI (95 mg, 0.496 mmol), and A4 (100 mg, 0.248 mmol) was stirred at room temperature for 10 mins under Ar. 4-aminomorpholine () (30.6 mg, 0.3 mmol) and DIPEA (130 mg, 0.992 mmol) were added to the reaction mixture successively. The mixture was stirred at RT for 12h. TLC (DCM: MeOH =10:1, Rf=0.4) showed the starting material was consumed completely. DCM (25 mL) was added to the reaction mixture and then the resulting mixture was poured into 30 mL water, and adjusted to pH 5'6 with aqueous citric acid (2N). The organic layer was separated and washed with water (20mL*2), dried over anhydrous Na2SO4, and concentrated. The residue was purified by preparative TLC to give product (36 mg, 29.7%) as a white solid. 1H NMR (400MHz, DMSO-d6) delta: 9.76 (s, 1H), 8.99 (s, 1H), 8.61'8.60 (d, 1H), 8.59 (d, 1H), 8.38'8.36 (m, 2H), 8.23'7.85 (m, 2H), 6.93 (s, 1H), 5.78 (s, 2H), 3.68 (s, 4H), 2.90 (s, 4H), 2.58 (s, 3H); LC-MS: m/z (ES+) for C24H22N8O4 487.15 [M+1]+.

suzuki reaction

Molecular Weight:137.61
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Exact Mass:137.0607417
Monoisotopic Mass:137.0607417
Topological Polar Surface Area:46.2
Heavy Atom Count:8
Complexity:65.1
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes