Sodium borohydride → HCID 58011549, compound

HRID 451945Notes

Reaction equation

HRID 451945 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C@@H:7]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=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+]>CO>[F:27][C:23]1[CH:22]=[C:21]([C@H: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]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:9]2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58011496HCID 58011496, compound

Product 1

HCID 58011549HCID 58011549, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 3-((R)-(2-ethoxy-2-oxoethoxy)(3-fluorophenyl)methyl)piperidine-1-carboxylate (29.88 g, 75.9 mmol) in MeOH (300 mL) was added NaBH4 (23 g, 605.2 mmol) in portions while the temperature was lower than 40° C. After addition, the mixture was stirred at rt for 2-3 hr. The solvent was removed in vacuo to give a residue which was partitioned between water and EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on silica gel chromatography to afford (R)-tert-butyl 3-((R)-(3-fluorophenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylate (11 g, 41%).

Workup

  1. customwas lower than 40° C
  2. additionAfter addition
  3. customThe solvent was removed in vacuo
  4. customto give a residue which
  5. customwas partitioned between water and EtOAc
  6. washThe organic layer was washed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified on silica gel chromatography

Sources & evidence

ORD record
ord-af13c96c93ec4169991739b94aa82f5d
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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