(Diethylamino)sulfur trifluoride → HCID 118207444, 화합물

HRID 1507222노트

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HRID 1507222 반응식
O[C@H:2]1[C@H:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.CCN(S(F)(F)[F:28])CC>C(Cl)Cl>[F:28][C@H:2]1[C@H:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 24820608Tert-butyl (3S,4S)-3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

생성물 1

HCID 118207444HCID 118207444, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3S,4S)-tert-butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate (400 mg, 1.36 mmol, the first eluting enantiomer E-1 from step E) in DCM (5 mL) cooled to 0° C. was added dropwise DAST (0.54 mL, 4.1 mmol) over 10 min. The mixture was allowed to warm up to rt and was stirred for 2 h. The reaction was slowly quenched with 50 mL of a 10% aqueous sodium bicarbonate solution and extracted four times with 50 mL of DCM. The combined organic layers were washed with 75 mL of brine, dried, and concentrated under vacuum to yield 390 mg of (3S,4S)-tert-butyl 3-fluoro-4-(4-hydroxyphenyl)piperidine-1-carboxylate which was used without further purification. LCMS (Method Q) RT 0.92 min, m/z 240.1 (M+H+).

후처리

  1. customThe reaction was slowly quenched with 50 mL of a 10% aqueous sodium bicarbonate solution
  2. extractionextracted four times with 50 mL of DCM
  3. washThe combined organic layers were washed with 75 mL of brine
  4. customdried
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-29e17b7b3f3e48faacfdf92390431a1b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221796B2

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