Sodium borohydride → (Meso-3aR,5r,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 2106153Notes

Reaction equation

HRID 2106153 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 20753133(Meso-3aR,5r,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-eda4506a8f3b4d89ad0979a077f5b403
Source dataset
uspto-grants-2009_08
Patent number
US07579473B2

Reaction notes

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