Sodium borohydride → tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 17743

Reaction equation

HRID 17743 reaction equation
[BH4-].[Na+].[C:3]([N:10]1[CH2:16][C@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][C@H:11]1[CH:12]=[O:13])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]>CO>[C:3]([N:10]1[CH2:16][C@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[CH2:14][C@H:11]1[CH2:12][OH:13])([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10969557tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 105%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (227 mg, 6 mmol) was added at 0° C. to a stirred solution of (2S,4R)-N-BOC-4-(t-butyldimethylsilyloxy)prolinaldehyde (522 mg, 1.58 mmol) in MeOH (10 mL), and the mixture was stirred at rt for 3 h. The reaction was quenched by adding sat. NaHCO3 (20 mL), and the resulting mixture was extracted with EtOAc (3×50 mL). The EtOAc extracts were washed with brine (2×50 mL), and dried (Na2SO4). The solvent was removed in vacuo to give (2S,4R)-N-BOC-4-(t-butyldimethylsilylhydroxy)prolinol (550 mg).

Workup

  1. customThe reaction was quenched
  2. additionby adding sat. NaHCO3 (20 mL)
  3. extractionthe resulting mixture was extracted with EtOAc (3×50 mL)
  4. washThe EtOAc extracts were washed with brine (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-50a57623f4c84a17a4ffdfa488dadd5b
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Linked notes

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