Sodium borohydride → (R)-tert-butyl 3-((3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate

HRID 451656Notes

Reaction equation

HRID 451656 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[O:6].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8]2)[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 46831638(R)-Tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate

Product 1

HCID 59201373(R)-tert-butyl 3-((3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate (10 g, 0.031 mol) in ethanol was added NaBH4 (4.71 g, 0.124 mol) portionwise. When the reaction was complete, the ethanol was distilled off, and water (100 mL) and EtOAc (100 mL) were added to the mixture. The organic phase was separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic phases ware washed with water, dried over Na2SO4 and concentrated to give (3R)-tert-butyl 3-((3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (9.1 g, 90%), which used without purification. 1H NMR (400 MHz, CDCl3): 1.24-1.45 (m, 4H), 1.46 (m, 9H), 1.61-1.68 (m, 1H), 1.73-1.84 (m, 1H), 3.05-3.26 (m, 2H), 3.55-3.66 (m, 1H), 3.82-3.96 (m, 1H), 4.42 (m, 1H), 7.20 (m, 1H), 7.27-7.30 (m, 2H), 7.32 (s, 1H). MS (E/Z): 326 (M+H+)

Workup

  1. distillationthe ethanol was distilled off
  2. additionwater (100 mL) and EtOAc (100 mL) were added to the mixture
  3. customThe organic phase was separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  5. washThe combined organic phases ware washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0edb778fb8d8447e862a1d1d6727e3d4
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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