Sodium borohydride → HCID 58460192, compound

HRID 1946491Notes

Reaction equation

HRID 1946491 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][N:12]2[C:16]3[C:17](=[O:20])[CH2:18][CH2:19][C:15]=3[N:14]=[C:13]2[CH:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][C:9]=1[Cl:10]>ClCCl.CO>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][N:12]2[C:16]3[CH:17]([OH:20])[CH2:18][CH2:19][C:15]=3[N:14]=[C:13]2[CH:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 58460220HCID 58460220, compound

Product 1

HCID 58460192HCID 58460192, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (155 mg) was added to a stirred solution of Intermediate 21 (660 mg) in dichloromethane (2 mL) and methanol (2 mL). The reaction mixture was stirred for 2.5 hours. More sodium borohydride (155 mg) was added. The RM was left stirring at room temp. under nitrogen for 1 hour. The reaction mixture was partitioned between EtOAc (50 ml) and water (30 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 title compound (660 mg). LC/MS MH+ 325, 327, Rt 1.63 min (5 minute run).

Workup

  1. waitThe RM was left
  2. stirringstirring at room temp. under nitrogen for 1 hour
  3. customThe reaction mixture was partitioned between EtOAc (50 ml) and water (30 ml)
  4. customThe two phases were separated
  5. extractionthe aqueous phase was extracted again with EtOAc (30 ml)
  6. customThe phases were separated
  7. customdried (hydrophobic frit)
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dcc5c54e620345cd9e32f799042f880a
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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