(Diethylamino)sulfur trifluoride → Tert-butyl 4-(4-bromo-1,3-thiazol-2-yl)-4-fluoropiperidine-1-carboxylate

HRID 1051649ノート

反応式

HRID 1051649 の反応式
C(N(S(F)(F)[F:7])CC)C.[Br:10][C:11]1[N:12]=[C:13]([C:16]2(O)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[S:14][CH:15]=1>ClCCl>[Br:10][C:11]1[N:12]=[C:13]([C:16]2([F:7])[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[S:14][CH:15]=1

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 66749307Tert-butyl 4-(4-bromo-1,3-thiazol-2-yl)-4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 66749859Tert-butyl 4-(4-bromo-1,3-thiazol-2-yl)-4-fluoropiperidine-1-carboxylate収率 78.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Diethylaminosulfur trifluoride (DAST) (0.083 mL, 0.627 mmol) was added to a 0° C. of tert-butyl 4-(4-bromothiazol-2-yl)-4-hydroxypiperidine-1-carboxylate (0.207 g, 0.570 mmol) in dichloromethane (2.8 mL). After 5 minutes, the cooling bath was removed and the reaction mixture was allowed to stir at room temperature overnight. Saturated aqueous sodium bicarbonate solution was added, and the aqueous phase was separated and extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 5-50% ethyl acetate-hexane) to afford tert-butyl 4-(4-bromothiazol-2-yl)-4-fluoropiperidine-1-carboxylate (0.163 g, 78%) as a colorless, waxy solid. MS (ESI, pos. ion) m/z 387, 389 [M+Na]+.

後処理

  1. customthe cooling bath was removed
  2. additionSaturated aqueous sodium bicarbonate solution was added
  3. customthe aqueous phase was separated
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 5-50% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-d738c4c4d31f4808ac0dc501c449f31e
出典データセット
uspto-grants-2016_07
特許番号
US09388161B2

反応ノート

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