(Diethylamino)sulfur trifluoride → Tert-butyl 3-cyano-3-fluoropiperidine-1-carboxylate

HRID 57582ノート

反応式

HRID 57582 の反応式
[C:1]([C:3]1(O)[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2].CCN(S(F)(F)[F:23])CC>C(Cl)Cl>[C:1]([C:3]1([F:23])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2]

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 58487593Tert-butyl 3-cyano-3-hydroxypiperidine-1-carboxylate

生成物 1

HCID 71114111Tert-butyl 3-cyano-3-fluoropiperidine-1-carboxylate収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of tert-butyl 3-cyano-3-hydroxypiperidine-1-carboxylate (5.7 g, 25.1 mmol) in DCM (50 mL) cooled to −78° C., DAST (4.85 g, 30.1 mmol) was added drop-wise and the resulting solution stirred at −78° C. for 1 hour. The reaction was warmed to 0° C. and stirred for an additional 1 hour. The reaction mixture was diluted with DCM and quenched with sat. aq. NaHCO3. The combined extracts were dried by Na2SO4, filtered and concentrated in vacuo to afford crude title compound as a pale yellow oil 5.5 g. MS (m/z): 129 (M+H-Boc)+

後処理

  1. temperatureThe reaction was warmed to 0° C.
  2. stirringstirred for an additional 1 hour
  3. customquenched with sat. aq. NaHCO3
  4. dry with materialThe combined extracts were dried by Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-17bb13e6850845719d534d377bf94c81
出典データセット
uspto-grants-2016_09
特許番号
US09434726B2

反応ノート

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