Sodium borohydride → HCID 46831646, compound

HRID 253549Notes

Reaction equation

HRID 253549 reaction equation
[C:1]([CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57419606Tert-butyl 3-benzoylpyrrolidine-1-carboxylate

Product 1

HCID 46831646HCID 46831646, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl 3-benzoylpyrrolidine-1-carboxylate (0.77 g, 2.8 mmol) in methanol (40 mL) was added granular NaBH4 (0.21 g, 5.6 mmol). The mixture was stirred at rt for 3 d and solvent was removed under reduced pressure. The residue was taken up in 5% aq HCl (50 mL) and extracted with ether (2×100 mL). The combined ether extracts were washed with satd aq NaHCO3 (25 mL) and dried over MgSO4. Removal of the solvent left tert-butyl 3-(hydroxy(phenyl)methyl)pyrrolidine-1-carboxylate (0.93 g, quant) as an oil.

Workup

  1. customsolvent was removed under reduced pressure
  2. extractionextracted with ether (2×100 mL)
  3. washThe combined ether extracts were washed with satd aq NaHCO3 (25 mL)
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent
  6. waitleft tert-butyl 3-(hydroxy(phenyl)methyl)pyrrolidine-1-carboxylate (0.93 g, quant) as an oil

Sources & evidence

ORD record
ord-19b28f4466a5405cb20487dcda0e6e21
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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