Methanol → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

HRID 1291239Notes

Reaction equation

HRID 1291239 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15](OCC)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[OH:21].[BH4-].[Li+].O>C(OCC)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:21])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 9993342Ethyl 1-((1,1-dimethylethoxy)carbonyl)-4-piperidineacetate

Product 1

HCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

In diethyl ether (20 ml) was dissolved ethyl N-tert-butoxycarbonyl-4-piperidineacetate (1.18 g) followed by addition of methanol (0.19 ml). Then, lithium borohydride (123 mg) was added under ice-cooling. The mixture was stirred at room temperature for 15 hours, after which time water was added under ice-cooling. The mixture was diluted with ethyl acetate, washed with aqueous NaCl solution, dried over MgSO4, and concentrated to provide the title compound as colorless oil (0.96 g). 1H-NMR (CDCl3) δ: 1.0-1.4(4H,m), 1.45(9H,s), 1.5-1.8(4H,m), 2.69(2H,t,J=13.3Hz), 3.6-3.8(2H,brm), 4.0-4.2(2H,brm).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. washwashed with aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eda3015640db4ae2b44020841b886716
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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