Ethyl (S)-2-(trifluoromethylsulfonyloxy)propionate → tert-Butyl 3-(1(R)-ethoxycarbonylethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176273Notes

Reaction equation

HRID 1176273 reaction equation
FC(F)(F)S([O:6][C@@H:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=O)=O.O[CH:17]1[CH:22]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])=[CH:25][CH:24]=2)[CH2:21][CH2:20][N:19]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:18]1>>[CH2:11]([O:10][C:8]([C@H:7]([O:6][CH:17]1[CH:22]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])=[CH:27][CH:28]=2)[CH2:21][CH2:20][N:19]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:18]1)[CH3:13])=[O:9])[CH3:12]

Participants

3

Reactant 2

HCID 11207429Ethyl (S)-2-(trifluoromethylsulfonyloxy)propionateHCID 15546933Tert-butyl 3-hydroxy-4-{4-[3-(2-methoxybenzyloxy) propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68632246tert-Butyl 3-(1(R)-ethoxycarbonylethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Procedure

Analogously to Example 35c, 0.32 ml of ethyl 2(S)-trifluoromethanesulphonyloxypropionate and 0.734 g of tert-butyl 3-hydroxy-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate are reacted. The title compound is obtained as a colourless oil. Rf=0.19 (1:3 EtOAc-heptane); Rt=5.93.

Sources & evidence

ORD record
ord-47472330c30347c19ac6e3041eccbc04
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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