Tetrahydrofuran → HCID 68501235, compound

HRID 1176271Notes

Reaction equation

HRID 1176271 reaction equation
C([C@:3]([O:8]S(C(F)(F)F)(=O)=O)([CH3:7])[C:4]([OH:6])=[O:5])C.[H-].[Na+].O[CH:19]1[CH:24]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])=[CH:27][CH:26]=2)[CH2:23][CH2:22][N:21]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:20]1.O1CC[CH2:54][CH2:53]1>>[CH2:53]([O:6][C:4]([C@@H:3]([O:8][CH:23]1[CH:24]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])=[CH:27][CH:26]=2)[CH2:19][CH2:20][N:21]([C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])[CH2:22]1)[CH3:7])=[O:5])[CH3:54]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 15546933Tert-butyl 3-hydroxy-4-{4-[3-(2-methoxybenzyloxy) propoxy]phenyl}piperidine-1-carboxylateHCID 86609988HCID 86609988, compound

Product 1

HCID 68501235HCID 68501235, compound

Procedure

0.32 ml of ethyl 2(R)-trifluoromethanesulphonyloxypropionic acid and 0.075 g of sodium hydride dispersion (55%) are added at −45° C. to the solution of 0.733 g of tert-butyl 3-hydroxy-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 5 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature over 5 hours and subsequently poured onto water. The mixture is extracted with ethyl acetate (2×). The combined organic phases are washed with brine, 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=0.26 (1:3 EtOAc-heptane); Rt=6.01.

Workup

  1. additionsubsequently poured onto water
  2. extractionThe mixture is extracted with ethyl acetate (2×)
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-678679f4994d451995d555f32fd9f253
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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