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

HRID 446714Notes

Reaction equation

HRID 446714 reaction equation
[O:1]=[C:2]1[CH2:16][C@@H:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@@H:4]2[CH2:3]1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]1[CH2:16][C@@H:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:8][C@@H:4]2[CH2:3]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 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1019 (4 g; 0.018 mole) was dissolved in 50 mL of ethanol. Sodium borohydride was added at RT portionwise. After stirring for 3 hours, the reaction was concentrated in vacuo. The resulting oil was dissolved in DCM (200 mL), washed with water, brine, (Na2SO4), and concentrated in vacuo to yield (3aR,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate as a yellow oil (Compound 1020, 3.79 g; 93% yield); 1H NMR (CDCl3): δ 4.2 (m, 1H), 3.55 (dd, 2H), 3.4 (dd, 2H), 2.7 (m, 2H), 2.2 (m, 2H), 1.6 (m, 2H), 1.5 (s, 9H).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe resulting oil was dissolved in DCM (200 mL)
  3. washwashed with water, brine, (Na2SO4),
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdf34d82b69745e7bb8e7b385814cb35
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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