Sodium borohydride → HCID 66671372, compound

HRID 2371107Notes

Reaction equation

HRID 2371107 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH:14]([C:22](=[O:37])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH:14]([CH:22]([OH:37])[CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:29][CH:30]=1)[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69246152HCID 69246152, compound

Product 1

HCID 66671372HCID 66671372, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound (100 mg) obtained from step 1 above in methanol (2 ml) at −10° C. to −2° C. was added sodium borohydride (9 mg) and stirred the mixture for 40 minutes at the same temperature. The solvent was evaporated under reduced pressure and the residue thus obtained was quenched with saturated solution of ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography using 5% methanol in dichloromethane as eluant to furnish the title compound (80 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue thus obtained
  3. customwas quenched with saturated solution of ammonium chloride
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-562b7f820b61495c93ffee83df936c6f
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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