Sodium borohydride → HCID 69890231, compound

HRID 2088121Notes

Reaction equation

HRID 2088121 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C@@H:15]2[C@@H:16]([C:18]#[N:19])[CH2:17][C@@:11]1([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12](=[O:20])[CH2:13][CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[C@@H:15]2[C@@H:16]([C:18]#[N:19])[CH2:17][C@@:11]1([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:12]([OH:20])[CH2:13][CH2:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69891696HCID 69891696, compound

Product 1

HCID 69890231HCID 69890231, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.8 g, 47 mmol) was added to a stirred, ice-cooled solution of (1R*,5S* 6S*)-8-benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octan-2-one (Description 40) in methanol (300 ml). The reaction mixture was stirred for 30 minutes, quenched with saturated aqueous NaHCO3 and extracted into ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate 0-20%) to give the title compound (31 g).

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted into ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate 0-20%)

Sources & evidence

ORD record
ord-b99e78441ea34ac585f01265904b9511
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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