Sodium borohydride → (1R*,2RS,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-en-2-ol

HRID 2088094Notes

Reaction equation

HRID 2088094 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C@@H:15]2[C@H:16]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH2:17][C@@:11]1([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12](=[O:27])[CH:13]=[CH: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]([S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:19])=[O:20])[CH2:17][C@@:11]1([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:12]([OH:27])[CH:13]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69686040(1R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-en-2-one

Product 1

HCID 69890698(1R*,2RS,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-en-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (450 mg, 11.8 mmol) was added to a stirred suspension of (1R*,5S*,6R*)-8-benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-en-2-one (Description 2; 3.5 g, 8.1 mmol) in methanol (40 ml) at +5° C. The reaction mixture was stirred for 1 hour and quenched with saturated NaHCO3 and concentrated in vacuo to removed methanol. The aqueous phase was extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated to give a 4.4:1 mixture of epimeric alcohols. The diastereoisomers were separated by flash chromatography followed by crystallisation.

Workup

  1. customquenched with saturated NaHCO3
  2. concentrationconcentrated in vacuo
  3. customto removed methanol
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×50 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customto give
  8. customThe diastereoisomers were separated by flash chromatography
  9. customfollowed by crystallisation

Sources & evidence

ORD record
ord-2e77547d53e14b80b4ba3b9ad46caf54
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

Loading…