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

HRID 2199174ノート

反応式

HRID 2199174 の反応式
[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

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 86660504tert-Butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylateHCID 178478994HCID 178478994、化合物

生成物 1

HCID 67468980tert-Butyl 4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  1. stirringThe reaction mixture was then stirred at room temperature for one hour
  2. customthe aqueous phase was separated off
  3. extractionAfter extraction of the aqueous phase with ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulphate
  5. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-263ff533434f4b51bb74d41ff2e49cb2
出典データセット
uspto-grants-2016_06
特許番号
US09357779B2

反応ノート

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