Ammonium Chloride → tert-Butyl 4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 2199174Notes

Reaction equation

[CH:1]1([CH2:7][Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CON(C)[C:13]([C:15]1[N:16]=[C:17]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[S:18][CH:19]=1)=[O:14].[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH:1]1([CH2:7][C:13]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]3)[S:18][CH:19]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: -78 °C

Procedure

Under argon and at −78° C., cyclohexylmethylmagnesium chloride 0.5M in diethyl ether (2.7 ml) was added dropwise to a solution of tert-butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (480 mg) in tetrahydrofuran (5 ml). The reaction mixture was stirred at −78° C. for one hour. The reaction mixture was then stirred at room temperature for one hour. 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-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (335 mg).

Workup

stirringThe reaction mixture was then stirred at room temperature for one hour
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-263ff533434f4b51bb74d41ff2e49cb2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09357779B2

Reaction notes

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