1-N-Boc-4-Piperidinecarboxylic acid methyl ester → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 481428Notes

Reaction equation

HRID 481428 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.CCCCCC.CCOCC>C1COCC1.Cl>[C:16]([N:13]1[CH2:14][CH2:15][CH:10]([CH2:9][OH:8])[CH2:11][CH2:12]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 21226445Aluminium lithium hydrideHCID 21584099Diethylether hexane

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

LAH (3.8 g, 100 mmol) was added portionwise to a solution the ester 2-3c (20.3 g, 83.5 mmol) in THF (300 mL) at 0° C. under argon. After the addition was complete, the mixture was stirred for 2 hours then poured onto ice, IN HCl was added and the slurry extracted 3× EtOAc. The organic layer was washed with water then brine, dried (MgSO4) and concentrated to give a white solid. The solid was swished with hexane/ether 9:1 and filtered to provide the alcohol 2-3.

Workup

  1. additionAfter the addition
  2. additionwas added
  3. extractionthe slurry extracted 3× EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. concentrationconcentrated
  7. customto give a white solid
  8. filtrationfiltered

Sources & evidence

ORD record
ord-a34edbcdf2834e8cb762e0a1bc9ca5da
Source dataset
uspto-grants-1998_08
Patent number
US05789421

Reaction notes

Loading…