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

HRID 891568ノート

反応式

HRID 891568 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-deeeaf3e388342b5bdd93e9333f99c92
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

読み込み中…