Methyl chloroformate → tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-{2-[2-(2-methoxycarbonylaminoethyl)phenoxy]ethoxy}piperidine-1-carboxylate

HRID 1176318Notes

Reaction equation

HRID 1176318 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:46]=[CH:45][CH:44]=[CH:43][C:5]=1[O:6][CH2:7][CH2:8][O:9][CH:10]1[CH:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[CH:18][CH:17]=2)[CH2:14][CH2:13][N:12]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:11]1.Cl[C:48]([O:50][CH3:51])=[O:49]>ClCCl.C(N(CC)CC)C>[CH3:35][O:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][O:26][CH2:25][CH2:24][CH2:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH:15]2[CH2:14][CH2:13][N:12]([C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])[CH2:11][CH:10]2[O:9][CH2:8][CH2:7][O:6][C:5]2[CH:43]=[CH:44][CH:45]=[CH:46][C:4]=2[CH2:3][CH2:2][NH:1][C:48]([O:50][CH3:51])=[O:49])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 68502787Tert-butyl 3-{2-[2-(2-aminoethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68501361tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-{2-[2-(2-methoxycarbonylaminoethyl)phenoxy]ethoxy}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

A solution of 0.25 g of tert-butyl 3-{2-[2-(2-aminoethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate (Example 56b) in 13 ml of dichloromethane and 0.12 ml of triethylamine is admixed at room temperature with a solution of 0.034 ml of methyl chloroformate in 1 ml of dichloromethane and stirred at room temperature over 2 hours. The reaction mixture is diluted with dichloromethane, washed with 1M potassium bisulphate solution (2×), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.15 (1:2 EtOAc-heptane); Rt=5.95.

Workup

  1. washwashed with 1M potassium bisulphate solution (2×)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-cdf587c677894f10a40530400d810b0c
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

Loading…