Sodium borohydride → HCID 69891916, compound

HRID 2088105Notes

Reaction equation

HRID 2088105 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C@@H:15]2[C@H:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@@:11]1([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:12](=[O:25])[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]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@@:11]1([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C@H:12]([OH:25])[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 69889518(1R*,5S*,6R*)-8-Benzyl-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octan-2-one

Product 1

HCID 69891916HCID 69891916, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (8.7 g, 0.23 mol) was added to a stirred suspension of (1R*,5S*,6R*)-8-benzyl-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octan-2-one (Description 19a; 76 g, 0.23 mol) in methanol (700 ml) at room temperature. The reaction mixture was stirred overnight, quenched with water and concentrated in vacuo. The residue was extracted into ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid.

Workup

  1. customquenched with water
  2. concentrationconcentrated in vacuo
  3. extractionThe residue was extracted into ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4da6a0903373461b86c4f77e2cfa8744
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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