Ethanol → 1-(4-Ethoxycarbonyl-1,3-thiazol-2-yl)4-methanesulfonyloxypiperidine

HRID 891568노트

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HRID 891568 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C.C(O)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:12][CH2:13][CH:14]([O:17][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:15][CH2:16]2)[S:9][CH:10]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22242823Ethyl 2-(4-hydroxypiperidin-1-yl)thiazole-4-carboxylate

생성물 1

HCID 865908511-(4-Ethoxycarbonyl-1,3-thiazol-2-yl)4-methanesulfonyloxypiperidine수율 49%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (128 mg, 0.50 mmol) (obtained as described in Reference Example 13(2)) in methylene chloride (6.5 ml) was added methanesulfonyl chloride (0.043 ml, 0.56 mmol) and triethylamine (0.084 ml, 0.60 mmol) in an ice bath. The reaction mixture was brought to room temperature in 10 minutes and then stirred for 30 minutes. After checking the completion of the reaction, ethanol (1 ml) was added thereto in an ice bath and then the reaction mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was recrystallized from a solution of ethyl acetate:n-hexane (5:1) to afford 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)4-methanesulfonyloxypiperidine (81.0 mg, yield 49%) as a white solid.

후처리

  1. additionwas added
  2. stirringin an ice bath and then the reaction mixture was stirred for 30 minutes
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was recrystallized from a solution of ethyl acetate:n-hexane (5:1)

출처 및 근거

ORD 기록
ord-deeeaf3e388342b5bdd93e9333f99c92
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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