Sodium borohydride → HCID 59598473, compound

HRID 2266249Notes

Reaction equation

HRID 2266249 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][CH:7]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=1)[C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)C.[BH4-].[Na+]>CCO>[F:27][C:23]1[C:22]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=2)=[C:21]([CH:7]([O:6][CH2:5][CH2:4][OH:3])[C@@H:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:9]2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59598458HCID 59598458, compound

Product 1

HCID 59598473HCID 59598473, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3R)-tert-butyl 3-((2-ethoxy-2-oxoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)piperidine-1-carboxylate (1.1 g, 2.3 mmol) in EtOH (20 mL) was added NaBH4 (0.7 g, 18.1 mmol) in portions. After addition, the mixture was stirred at rt overnight. TIc showed the start 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, filtered and evaporated to give (3R)-tert-butyl 3-((6-fluoro-3′-methylbiphenyl-2-yl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylate (1 g, 99%) 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. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-781d3e52b66d4ea8988662ebc79a9d04
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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