Ethanol → tert-Butyl 4-[4-(2-cyclohexyl-N-methoxyethanimidoyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 2199177Notes

Reaction equation

HRID 2199177 reaction equation
[Cl-].CO[NH3+].[CH3:5][O:6][N:7](C)[C:8]([C:10]1[N:11]=[C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[S:13][CH:14]=1)=O.O.[CH2:30](O)[CH3:31]>>[CH:30]1([CH2:31][C:8]([C:10]2[N:11]=[C:12]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[S:13][CH:14]=2)=[N:7][O:6][CH3:5])[CH2:19][CH2:20][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 11639O-methylhydroxylammonium chlorideHCID 86660504tert-Butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Product 1

HCID 86660506tert-Butyl 4-[4-(2-cyclohexyl-N-methoxyethanimidoyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

Conditions

Temperature
50 °C

Procedure

At room temperature, methoxyammonium chloride (171 mg) was added to a solution of tert-butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (403 mg) in ethanol (2 ml). The reaction mixture was stirred at 50° C. for 24 hours, and water was then added. The aqueous phase was separated off and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified chromatographically. This gave tert-butyl 4-[4-(2-cyclohexyl-N-methoxyethanimidoyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (361 mg).

Workup

  1. customThe aqueous phase was separated off
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-3ae44a1cde364a1eae928f090857ef4c
Source dataset
uspto-grants-2016_06
Patent number
US09357779B2

Reaction notes

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