Sodium borohydride → HCID 58460144, compound

HRID 1946486Notes

Reaction equation

HRID 1946486 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3[C:16](=[O:19])[CH2:17][CH2:18][C:14]=3[N:13]=[C:12]2[CH:20]([CH3:22])[CH3:21])=[CH:6][CH:5]=1>ClCCl.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]2[C:15]3[CH:16]([OH:19])[CH2:17][CH2:18][C:14]=3[N:13]=[C:12]2[CH:20]([CH3:22])[CH3:21])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58460235HCID 58460235, compound

Product 1

HCID 58460144HCID 58460144, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (76 mg) was added to a stirred solution of Intermediate 18 (290 mg) in dichloromethane (3 ml) and methanol (3 ml). The reaction mixture was stirred for 3 hours. The reaction mixture was concentrated under vacuum, partitioned between EtOAc (20 ml) and water (15 ml). The two phases were separated and the aqueous phase was extracted again with EtOAc (2×10 ml). The phases were separated, the organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum to give the title compound (272 mg). LC/MS MH+ 291, Rt 1.35 min (5 minute run).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompartitioned between EtOAc (20 ml) and water (15 ml)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted again with EtOAc (2×10 ml)
  5. customThe phases were separated
  6. customdried (hydrophobic frit)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9e5628abad7444c0994aa0f1ba2efdba
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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