Triethylamine → Tert-butyl 4-hydroxypiperidine-1-carboxylate

HRID 1670623Notes

Reaction equation

HRID 1670623 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(N(CC)CC)C>ClCCl>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add sodium borohydride (0.82 mol, 31.3 g) in portions to a solution of 1-(tert-butoxycarbonyl)-4-piperidone (0.74 mol, 150 g) and triethylamine (1.5 mol, 151.6 g) in dichloromethane (1 L) at 0° C. Upon complete addition, warm the reaction mixture to room temperature and stir for 4 h. Quench the reaction mixture with saturated ammonium chloride solution and remove the ethanol under reduced pressure. Dissolve the residue in water and extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (150 g, 99%) as a viscous solid. 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 1.53 (d, 2H), 1.83-1.87 (m, 2H), 3.02 (dt, 2H), 3.8-3.85 (m, 3H).

Workup

  1. additionUpon complete addition
  2. customQuench the reaction mixture with saturated ammonium chloride solution
  3. customremove the ethanol under reduced pressure
  4. dissolutionDissolve the residue in water
  5. extractionextract with dichloromethane
  6. dry with materialDry the organic layer over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-649be104a8e94be5b12b5ada2d54c520
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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