Ethanol → 4-t-Butyidimethylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine

HRID 891570ノート

反応式

HRID 891570 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])CC2)[S:9][CH:10]=1)=[O:5])[CH3:2].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1.C(O)C>CN(C)C=O>[Si:18]([O:17][CH:14]1[N:11]([C:8]2[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[CH2:16][CH2:15]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

参加物

6

反応物 4

HCID 702EthanolHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22242823Ethyl 2-(4-hydroxypiperidin-1-yl)thiazole-4-carboxylate

生成物 1

HCID 178581074-t-Butyidimethylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine収率 103.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (1.00 g, 3.90 mmol) (obtained as described in Reference Example 13(2)) in dimethylformamide (50 ml) were added t-butyldimethylsilyl chloride (1.2 g, 7.96 mmol) and imidazole (0.6 g, 8.8 mmol) in an ice bath. The reaction mixture was brought to room temperature in 10 minutes and then stirred for 18 hours. After checking the completion of the reaction, ethanol was added thereto in an ice bath, and the reaction mixture was then stirred at room temperature 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 purified by chromatography on a silica gel column using n-hexane:ethyl acetate (4:1) as the eluant to afford 4-t-butyidimethylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine (1.38 g, yield 95%) as a pale yellow oil.

後処理

  1. additionwas added
  2. stirringin an ice bath, and the reaction mixture was then stirred at room temperature 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 purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-778c6a79c9f142388523203c3f65e571
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

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