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

HRID 57582노트

반응식

HRID 57582 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 71114111Tert-butyl 3-cyano-3-fluoropiperidine-1-carboxylate수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-17bb13e6850845719d534d377bf94c81
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434726B2

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