Sodium borohydride → HCID 21893458, compound

HRID 1358649Notes

Reaction equation

HRID 1358649 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10783725HCID 10783725, compound

Product 1

HCID 21893458HCID 21893458, compoundYield 357.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.5 g (1.45 mmol) of the material from Example 45 and 0.055 g (1.45 mmol) of sodium borohydride in 5 mL of ethanol was stirred overnight at room temperature, then concentrated in vacuo. The residue was partitioned between 25 mL of water and 25 mL of ethyl acetate, the organic layer separated and the aqueous layer extracted three more times with 25 mL each of ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Chromatography (25 g of silica gel, 60% ethyl acetate/hexane) of the residue afforded 1.8 g (71%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 25 mL of water and 25 mL of ethyl acetate
  3. customthe organic layer separated
  4. extractionthe aqueous layer extracted three more times with 25 mL each of ethyl acetate
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a9f33078ac747f68907c30c9ede9af3
Source dataset
uspto-grants-2003_07
Patent number
US06596716B2

Reaction notes

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