Sodium borohydride → HCID 15078286, compound

HRID 982466Notes

Reaction equation

HRID 982466 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C@@H:23]([OH:40])[CH2:24][CH2:25][C:26]([C:28]2[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=2)=[O:27])[CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])(=[O:4])=[O:3].[BH4-].[Na+]>C1COCC1.CO.C(OCC)(=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C@@H:23]([OH:40])[CH2:24][CH2:25][CH:26]([C:28]2[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=2)[OH:27])[CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])(=[O:3])=[O:4]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 10008259HCID 10008259, compound

Product 1

HCID 15078286HCID 15078286, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

35 g of (-)-(1S)-1-(3-methylsulfonyl-4-n-propoxy-5-benzyloxyphenyl)-4-(3,4,5-trimethoxyphenyl)butan-1-ol-4-one (STEP E) dissolved in a mixture of 300 mL dry THF and 100 mL of methanol was treated with 3.5 g of NaBH4 at 0° C. and stirred for 3 h. The reaction mixture was then allowed to gradually warm to room temperature and stirring was continued for additional 2 h. After the completion of the reaction, the solvent was evaporated at reduced pressure and the residue obtained as such was redissolved in 300 ml of ethyl acetate. The organic layer was washed with 1.5N HCl, distilled water and brine respectively, and then dried over MgSO4 and evaporated to yield a colorless syrup which was used without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for additional 2 h
  3. customAfter the completion of the reaction
  4. customthe solvent was evaporated at reduced pressure
  5. customthe residue obtained
  6. washThe organic layer was washed with 1.5N HCl
  7. distillationdistilled water and brine respectively
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. customto yield a colorless syrup which
  11. customwas used without further purification

Sources & evidence

ORD record
ord-f20e24ae49c7485e9fe2dbb796b54487
Source dataset
uspto-grants-1991_02
Patent number
US04996203

Reaction notes

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