Tert-butyl 3-[2-(2-hydroxymethylphenoxy)ethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate → tert-Butyl 3-{2-[2-(2-hydroxypropoxymethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1712495Notes

Reaction equation

HRID 1712495 reaction equation
[OH:1][CH2:2][C:3]1[CH:45]=[CH:44][CH:43]=[CH:42][C:4]=1[O:5][CH2:6][CH2:7][O:8][CH:9]1[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[CH:17][CH:16]=2)[CH2:13][CH2:12][N:11]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:10]1>CN(C)C=O.C1O[C@H]1C.N12CCN(CC1)CC2.Cl>[OH:5][CH:4]([CH3:42])[CH2:3][O:1][CH2:2][C:3]1[CH:45]=[CH:44][CH:43]=[CH:42][C:4]=1[O:5][CH2:6][CH2:7][O:8][CH:9]1[CH:14]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[CH:19][CH:20]=2)[CH2:13][CH2:12][N:11]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[CH2:10]1

Participants

6

Reactant 1

HCID 68501214Tert-butyl 3-[2-(2-hydroxymethylphenoxy)ethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68499007tert-Butyl 3-{2-[2-(2-hydroxypropoxymethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 4

HCID 9237DabcoCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 146262(2S)-2-MethyloxiraneSolvent

Procedure

A solution of 0.34 g of tert-butyl 3-[2-(2-hydroxymethylphenoxy)ethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 10 ml of N,N-dimethylformamide and 0.39 ml of (S)-(−)-propylene oxide (plus 0.3 ml after 2.5 hours, 1.0 ml after 5 hours) and one drop of 1,4-diazabicyclo[2.2.2]octane is stirred at 100° C. over 26 hours. The reaction mixture is cooled, diluted with 1N HCl and extracted with ethyl acetate (2×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.38 (2:1 EtOAc-heptane); Rt=5.88.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0ffb1b941b0f46718e6d3f0b8243bfb0
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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