BOC-OIC-OH

White to off-white powder

L-octahydroindole-2-carboxylic acid (1.69 g, 10 mmol) was added to the reaction flask, Add 30 mL of THF and 30 mL of distilled water to stir, A 7 mL aqueous solution of NaOH (0.68 g, 17 mmol) was added dropwise to the ice bath, Plus, The reaction was stirred for 10 min.(Boc) 2O (2.84 g, 13 mmol)Rose to room temperature for 12h.TLC detection reaction is completed, diluted with water, with methyl tert-butyl ether extraction impurity removal, The water phase with citric acid PH to acidic, Ethyl acetate was extracted three times, the organic phases were combined, washed with saturated brine, dried over Na2SO4, Filtration and concentration gave 3.21 g of compound 1 in 100percent yield.Triethylamine (8.25 mL, 59 mmol) was added to (S)-octahydroindole-2- carboxylic acid (10.0 g, 59 mmol) in a 1/1 volume/volume mixture of tetrahydrofuran/water (200 ML total), followed by addition of di-tert-butyl dicarbonate (14.0 g, 65 mmol). The reaction mixture was stirred overnight at room temperature, and then concentrated with no heating to remove tetrahydrofuran. The aqueous mixture was partitioned between ethyl acetate (300 mL), water (100 mL), and citric acid solution (50 ML, 10percent aqueous). The layers were separated, the organic layer washed with brine (50 mL), dried (magnesium sulfate), filtered and concentrated to an oil, which solidified on standing. The solid was slurried in hexanes and collected by filtration. 15.63 g, 98percent. MS (APCI-) 17 1/Z (percent): 268 (100). Calcd for C14H23NO4 : C, 62.43 ; H, 8.61 ; N, 5.20 Found: C, 62.33 ; H, 8.30 ; N, 5.15To a stirred solution of (2S, 3aS, 7AS)-OCTAHYDROINDOLE-2-CARBOXYLIC acid (30 g, 0.18 mol) in dioxane (180 ML) and 1 M NAOH (180 mL), was added di- TE7X-BUTYL DICARBONATE (48 G, 0. 22 mol). The reaction mixture was stirred for 18 hours at room temperature and then diluted with diethyl ether (500 mL) and water (500 mL). The resulting aqueous layer was removed and cooled to 0 °C. Methylene chloride (1 L) was added, and the mixture adjusted to pH 3 by the addition of 2 M HC1. The organic layer was removed and the aqueous phase extracted with methylene chloride (2 x 25Q ML). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford A colorless oil. Trituration with ether and hexanes followed by removal of the excess solvents afforded the desired (2S, 3aS, 7AS)-OCTAHYDROINDOLE-1, 2- dicarboxylic acid 1-TERT-BUTYL ester (4 6. 3 g, 97percent), as a white solid : NNM (300 MHz, DMSO-d6) 8 1.00-1. 70 (m, 7H), 1.32, 1.38 (2 s, 9H), 1.76-1. 98 (m, 2H), 2.01-2. 13 (m, 1H), 2.18-2. 33 (m, 1H), 3.59-3. 69 (m, 1H), 3. 99-4. 10 (m, 1H); MS (CI) 170 [M + H-100 (Boc)] +, 270 [M + H] +.(a) To a stirred solution of (2R, 3aS, 7aS)-octahydro-lH-indole-2-carboxylic acid (250 g, 1.0 equiv) (1) in THF (3 L) and water (1.5 L) at 0 °C was added dropwise a cooled aqueous solution of 2.5 M NaOH (1 L). The reaction mixture was stirred for 15 minutes at the same temperature. Di-tert-butyl dicarbonate (1.3 equiv) was added dropwise, maintaining the temperature at 0 °C. The resulting reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was washed with MTBE (3 times). The aqueous phase was acidified with IM aqueous citric acid and extracted with ethyl acetate (3 times). The combined organic layers were dried over sodium sulfate and concentrated to dryness to afford (2R, 3a, S', 7a

Molecular Weight:269.34
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:269.16270821
Monoisotopic Mass:269.16270821
Topological Polar Surface Area:66.8
Heavy Atom Count:19
Complexity:374
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes