Sodium borohydride → HCID 59598495, compound

HRID 2266247Notes

Reaction equation

HRID 2266247 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:15]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[O:16])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[C:6]([CH:15]([OH:16])[C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:18]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59598486HCID 59598486, compound

Product 1

HCID 59598495HCID 59598495, compoundYield 139.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 3-(6-fluoro-3′-methylbiphenylcarbonyl)piperidine-1-carboxylate (3.5 g, 6.29 mmol) in MeOH (50 mL) was added NaBH4 (0.95 g, 25 mmol) in portions at rt. After addition, the mixture was stirred for 2 h. Tlc showed the starting material had disappeared. The solvent was removed in vacuo to leave a residue which was partitioned between water and EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4 and evaporated to give (3R)-tert-butyl 3-((6-fluoro-3′-methylbiphenyl-2-yl)(hydroxy)methyl)piperidine-1-carboxylate (3.5 g, 100%), which was used in the next step without purification.

Workup

  1. additionAfter addition
  2. customThe solvent was removed in vacuo
  3. customto leave a residue which
  4. customwas partitioned between water and EtOAc
  5. washThe organic layer was washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-de4b5d46774d47228995b78f6dba8e3a
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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