tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-hydroxypiperidine-1-carboxylate

HRID 1779075Notes

Reaction equation

HRID 1779075 reaction equation
[BH4-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]>CO.O.[Cl-].[Na+].O>[OH:16][CH:13]1[CH2:12][CH2:11][N:10]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:15][CH2:14]1

Participants

6

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.95 g, 25 mmol) was added to a solution of 1-Boc-4-piperidone (2.50 g, 12.5 mmol) in MeOH (25 mL) at 0° C. The resulting mixture was stirred at 0° C. for 2 hours, then room temperature for 2 hours. The mixture was diluted with water (100 mL) and brine (100 mL) then extracted with EtOAc (2×150 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to give the title compound A110 as a thick colorless oil (2.47 g, 98%); 1H NMR (400 MHz, CDCl3) δ 3.91-3.79 (m, 3H), 3.02 (m, 2H), 1.93-1.78 (m, 2H), 1.56 (d, J=4.2 Hz, 1H), 1.52-1.40 (m, 11H).

Workup

  1. waitroom temperature for 2 hours
  2. extractionthen extracted with EtOAc (2×150 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78b2849e13e64150985b03dbf913d9c7
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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