Tetrahydrofuran → Benzyl 4-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 2209457Notes

Reaction equation

HRID 2209457 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.C1COCC1.C(N(C(C)C)CC)(C)C.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C(OCC)(=O)C>[C:25]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 739534-PiperidineethanolHCID 81531Diisopropylethylamine

Product 1

HCID 13971210Benzyl 4-(2-hydroxyethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-piperidineethanol 8 (15 g, 0.12 mol), THF (500 mL), and diisopropylethylamine (40.5 mL, 0.23 mol) at 0° C. was added benzyl chloroformate (16.5 mL, 0.12 mmol). After 1 h at 0° C. the reaction mixture was diluted with ethyl acetate and then washed with H2O (2×), 10% KHSO4, and brine, dried (MgSO4), and concentrated to give 112 as a colorless oil.

Workup

  1. washwashed with H2O (2×), 10% KHSO4, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-022edb4bea5d42c9844451ca0b1c362c
Source dataset
uspto-grants-1995_10
Patent number
US05455243

Reaction notes

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