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

HRID 1198498Notes

Reaction equation

HRID 1198498 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. TLC Rf=0.60 (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.35 (m, 5H), 5.13 (s, 2H), 4.18 (m, 2H), 3.70 (q, J=7 Hz, 2H), 2.80 (m, 2H), 1.80-1.50 (m, 5H), 1.19 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-88d4aae2f7424895af5eed6781f6b248
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

Loading…