Sodium borohydride → HCID 67751644, compound

HRID 2210684Notes

Reaction equation

HRID 2210684 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][N:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:19]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C@H:8]2[C@@H:12]([OH:13])[CH2:11][CH2:10][N:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19379393HCID 19379393, compound

Product 1

HCID 67751644HCID 67751644, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(diphenylmethyl)-1-ethoxycarbonylpyrrolidin-3-one (Example 1c, 5.75 g, 18 mmol) in ethanol (50 ml) was added sodium borohydride (1.00 g, 26 mmol) and the mixture was stirred under nitrogen for 60 h at room temperature. The reaction mixture was partitioned between 10% citric acid/ethyl acetate, the organic phase washed with saturated brine and dried (MgSO4). The solvent was removed in vacuo and the residue chromatographed on silica gel using ethyl acetate/hexane (2:3) as eluant. Recrystallisation from ethyl acetate/hexane gave cis-2-(diphenylmethyl)-3-hydroxy-1-ethoxycarbonylpyrrolidine, m.p.=104°-105° C. 1H NMR (360 MHz, CDCl3) δ7.00-7.50 (10H, m), 4.78 (1H, dd, J=9 Hz and J=7 Hz), 4.46 (1H, dd, J=8.0 Hz and J=7.0 Hz), 4.32 (1H, d, J=9 Hz), 3.83 (2H, m), 3.47 (2H, m), 3.31 (1H, m), 2.10 (1H, m), 1.95 (1H, m), 1.00 (3H, t, J=7.0 Hz).

Workup

  1. customThe reaction mixture was partitioned between 10% citric acid/ethyl acetate
  2. washthe organic phase washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo
  5. customthe residue chromatographed on silica gel
  6. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c6b458f936b14d87a6b97428d1476417
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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