Sodium borohydride → HCID 58460153, compound

HRID 1946502Notes

Reaction equation

HRID 1946502 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[C:20]([CH3:23])([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[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58460143HCID 58460143, compound

Product 1

HCID 58460153HCID 58460153, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (158 mg) was added to a stirred solution of Intermediate 33 (421 mg) in dichloromethane (3 ml) and methanol (3.00 ml). The reaction mixture was stirred for 16 hours. The reaction mixture was concentrated under vacuum, partitioned between EtOAc (40 ml) and water (40 ml). The two phases were separated and the aqueous phase was extracted again with EtOAc (30 ml). The phases were separated, the organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum to give the required product (404 mg). LC/MS MH+ 305, Rt 2.59 min (5 minute run).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompartitioned between EtOAc (40 ml) and water (40 ml)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted again with EtOAc (30 ml)
  5. customThe phases were separated
  6. customdried (hydrophobic frit)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-422345f54d714dfe98f1fe1bf4d850c9
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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