Sodium borohydride → (1R*,2R*,5S*,6R*)-8-Benzyl-1-(4-fluorophenyl)-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol

HRID 2088100Notes

Reaction equation

HRID 2088100 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:15][C@@:9]1([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:10](=[O:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:17])=[O:18])[CH2:15][C@@:9]1([C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[C@H:10]([OH:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69889540(1R*,5S*,6R*)-8-Benzyl-1-(4-fluorophenyl)-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-one

Product 1

HCID 69891767(1R*,2R*,5S*,6R*)-8-Benzyl-1-(4-fluorophenyl)-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-olYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R*,5S*,6R*)-8-Benzyl-1-(4-fluorophenyl)-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-one (Description 13; 11.65 g, 25.95 mmol) was stirred in methanol (100 ml) then sodium borohydride (981 mg, 25.95 mmol) added and the mixture stirred at room temperature for 2 hours. The reaction mixture was quenched with water then concentrated in vacuo and partitioned between water and ethyl acetate. The organics were collected, dried (MgSO4), and concentrated in vacuo to give a cream solid which was triturated in diethyl ether and filtered to give the title compound as a cream-coloured solid (7.26 g, 62%).

Workup

  1. customThe reaction mixture was quenched with water
  2. concentrationthen concentrated in vacuo
  3. custompartitioned between water and ethyl acetate
  4. customThe organics were collected
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a cream solid which
  8. customwas triturated in diethyl ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-f5007ca677b64a9fab57a98f58868b97
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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