Sodium borohydride → HCID 15087635, compound
Reaction equation
[OH:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])/[CH:3]=[CH:4]/[CH:5]=[CH:6]/[C:7]1[S:11][C:10]([C:12](=[O:20])[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:9][CH:8]=1.[BH4-].[Na+]>CO>[OH:20][CH:12]([C:10]1[S:11][C:7](/[CH:6]=[CH:5]/[CH:4]=[CH:3]/[CH:2]([OH:1])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:8][CH:9]=1)[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Into 3 ml of methanol was dissolved 50 mg of the titled product of Example 28. The methanol solution was cooled to 0° C. (ice bath) and 5 mg of NaBH4 was added. The reaction mixture was stirred for 1 hour at 0° C. and then quenched with acetone. The solvent was removed from the quenched reaction mixture under reduced pressure. Water was added to the residue and it was extracted 3x with ethyl acetate. The combined extracts were dried MgSO4, filtered and the solvent removed under reduced pressure. The oily residue was chromatographed on a silica gel column. Elution with 3:7 ethyl acetate:hexane produced 35 mg of the titled product as a light yellow oil.
Workup
- additionwas added
- customquenched with acetone
- customThe solvent was removed from the quenched reaction mixture under reduced pressure
- additionWater was added to the residue and it
- extractionwas extracted 3x with ethyl acetate
- filtrationfiltered
- customthe solvent removed under reduced pressure
- customThe oily residue was chromatographed on a silica gel column
- washElution with 3:7 ethyl acetate
Sources & evidence
- ORD record
- ord-93a9d55a51814080a01c168da1057aa4
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04970234
Reaction notes
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