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

HRID 260130Notes

Reaction equation

HRID 260130 reaction equation
C([N:4]([CH:7]([CH3:9])C)[CH2:5][CH3:6])(C)C.[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([O:17][C:18]([N:4]1[CH2:5][CH2:6][CH:12]([CH2:11][CH2:10][OH:17])[CH2:9][CH2:7]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 81531Diisopropylethylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-1 (Aldrich) (25 g, 0.94 mol) in THF (400 mL) was treated with diisopropylethylamine (67 mL, 0.388 mol) and cooled to 0° C. under argon. Benzylchloroformate (27.6 mL, 0.194 mol) was added and the reaction was allowed to warm to room temperature. The reaction was concentrated, the residue was diluted with Et2O (300 mL), washed with water, 10% KHSO4 solution and brine, dried (MgSO4), filtered and evaporated to give 3-2 as an oil. Rf (35% EtOAc/Hexanes) 0.08 1H NMR (300 MHz, CDCl3) δ 7.38 (s, 5H), 5.13 (s, 2H), 4.18 (b, 2H), 3.7 (dd, 2H), 2.8 (bt, 2H), 1.78 (bd, 2H), 1.5 (m, 2H), 1.4 (m, 1H), 1.2 (m, 2H).

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe reaction was concentrated
  3. additionthe residue was diluted with Et2O (300 mL)
  4. washwashed with water, 10% KHSO4 solution and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-87284058b9184cad88c730918007fad9
Source dataset
uspto-grants-1996_06
Patent number
US05525617

Reaction notes

Loading…