Sodium borohydride → 1-Boc-3-Cyano-4-hydroxypyrrolidine

HRID 639105Notes

Reaction equation

HRID 639105 reaction equation
[C:1]([C:3]1(C)[C:7](=[O:8])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2].[BH4-].[Na+]>CCO>[C:1]([CH:3]1[CH:7]([OH:8])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 56970590HCID 56970590, compound

Product 1

HCID 107985871-Boc-3-Cyano-4-hydroxypyrrolidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-cyano-3-methyl-4-oxo-1-pyrrolidinecarboxylate (2.3 g, 10.2 mmol) in EtOH (100 mL) at 0° C. was added NaBH4 (775 mg, 20.5 mmol) portion-wise. After 30 min., the solution was concentrated and the residue partitioned between H2O-DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried (Na2SO4), concentrated and purified by column chromatography (silica, 1% MeOH in DCM (1% NH4OH)) affording the title compound as a yellow oil: LCMS (ES) m/e 227 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue partitioned between H2O-DCM
  3. washThe aqueous phase was washed several times with DCM
  4. dry with materialthe combined organic fractions were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica, 1% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-5aaa44df60d34786b30fb81b6d432ab8
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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