Potassium tert-butoxide → HCID 77506156, compound

HRID 1176455Notes

Reaction equation

HRID 1176455 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([S:47]([C:50]1[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=1)(=[O:49])=[O:48])[CH2:9][CH:10]([OH:46])[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:14]1.CC(C)([O-])C.[K+]>O1CCCC1.Cl>[CH3:38][O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][O:29][CH2:28][CH2:27][CH2:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH:18]2[CH2:17][CH2:16][N:15]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:14][CH:13]2[O:12][CH2:11][CH:10]2[CH2:9][N:8]([S:47]([C:50]3[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=3)(=[O:49])=[O:48])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:46]2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 68504601HCID 68504601, compound

Product 1

HCID 77506156HCID 77506156, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.04 g tert-butyl 3-{3-[(2-fluorophenyl)(toluene-4-sulphonyl)amino]-2(R,S)-hydroxypropoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 0.60 g of potassium tert-butoxide in 30 ml of tetrahydrofuran is stirred at reflux over 30 minutes. The reaction mixture is cooled to room temperature, 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 colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.30 (1:2 EtOAc-heptane); Rt=6.32.

Workup

  1. temperatureat reflux over 30 minutes
  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-2d651f5f3d0b4b51a4d6de577692880b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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