Isopropyl chloroformate → HCID 57930058, compound

HRID 423458Notes

Reaction equation

HRID 423458 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1.C(N(CC)CC)C>C(Cl)Cl>[OH:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 4207714-Piperidinemethanol

Product 1

HCID 57930058HCID 57930058, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropyl chloroformate (1.0M in toluene, 43.4 mL, 43.4 mmol) was added dropwise to a mixture of 4-piperidinemethanol (5 g, 43.4 mmol) and triethylamine (12.1 mL, 86.8 mmol) in CH2Cl2 (150 mL) at 0° C. over 20 min. The mixture was stirred at ambient temperature overnight. The mixture was washed with water, followed by brine. The organic layer was separated and dried over MgSO4, filtered, and the filtrate was concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 5% MeOH/CH2Cl2 to give 7.76 g (89%) of 1-methylethyl 4-(hydroxymethyl)-1-piperidinecarboxylate as a clear oil. 1H NMR (400 MHz, CDCl3): δ 4.93-4.78 (m, 1H), 4.19-4.09 (m, 2H), 3.47 (d, 2H, J=6.2 Hz), 2.75-2.65 (m, 2H), 1.75-1.56 (m, 3H), 1.21 (d, 6H, J=6.2 Hz), 1.17-1.06 (m, 2H); LRMS (ESI), m/z 202 (M+H).

Workup

  1. washThe mixture was washed with water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-5082b3ef1567415bb35fafafa5709175
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

Loading…