Ammonium Chloride → HCID 67468382, compound

HRID 1506587Notes

Reaction equation

Cl[Mg][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:11]([C:13]1[N:14]=[C:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[S:16][CH:17]=1)=[O:12].[Cl-].[NH4+]>O1CCCC1>[OH:12][CH:11]([C:13]1[N:14]=[C:15]([CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]2)[S:16][CH:17]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Under an argon atmosphere and at −78° C., chloro(2-phenylethyl)magnesium (1M in diethyl ether, 3.77 ml) was added dropwise to a solution of tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (1.0 g) in tetrahydrofuran (10 ml). The reaction mixture was stirred at −78° C. for one hour, and more chloro(2-phenylethyl)magnesium (3M in diethyl ether, 0.20 ml) was then added dropwise. The reaction mixture was then stirred for 20 minutes. Saturated ammonium chloride solution was then added to the reaction mixture, and the aqueous phase was separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. This gave tert-butyl 4-[4-(1-hydroxy-3-phenylpropyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (790 mg).

Workup

stirringThe reaction mixture was then stirred for 20 minutes
customthe aqueous phase was separated off
extractionAfter extraction of the aqueous phase with ethyl acetate
dry with materialthe combined organic phases were dried over sodium sulphate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-4d31ca34264446a4b6c8179dee88bbda
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09220266B2

Reaction notes

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