Sodium borohydride → rac-tert-butyl (3aR,5R,6aS)-5-hydroxy-octahydrocyclopenta(c)pyrrole-2-carboxylate

HRID 1011325노트

반응식

HRID 1011325 반응식
[BH4-].[Na+].[O:3]=[C:4]1[CH2:18][C@@H:7]2[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C@@H:6]2[CH2:5]1>CO>[OH:3][CH:4]1[CH2:18][C@@H:7]2[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:10][C@@H:6]2[CH2:5]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 10998692cis-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester

생성물 1

HCID 20753133rac-tert-butyl (3aR,5R,6aS)-5-hydroxy-octahydrocyclopenta(c)pyrrole-2-carboxylate수율 98%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Sodium borohydride (0.15 g, 4.00 mmol), was added to a solution of 1,1-dimethylethyl (3aR,6aS)-5-oxo-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (0.45 g, 2.00 mmol) in 10 mL methanol at 0° C. and the reaction mixture was stirred for 1 h at this temperature. The solvent was evaporated, the crude mixture was diluted with 100 mL ethyl acetate and washed with water (30 mL), 1M aqueous hydrochloric acid and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give 1,1-dimethylethyl (3aR,6aS)-5-(hydroxy)-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (0.44 g, 98%). 1H NMR (400 MHz, d6-DMSO): 4.08 (m, 1H), 3.40 (m, 2H), 3.30 (m, 2H), 2.50 (m, 2H), 1.98 (m, 2H), 1.40 (s, 9H), 1.30 (m, 2H). MS (EI) for C12H21NO3: 228 (MH+).

후처리

  1. customThe solvent was evaporated
  2. additionthe crude mixture was diluted with 100 mL ethyl acetate
  3. washwashed with water (30 mL), 1M aqueous hydrochloric acid and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-369b8b67bb244e81a607e901017fa978
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977345B2

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