홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

(Diethylamino)sulfur trifluoride → (2R,4S)-tert-butyl 4-fluoro-2-(3-fluorophenyl)pyrrolidine-1-carboxylate

HRID 513006
노트
인쇄 미리보기

반응식

HRID 513006 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][C@@H:11](O)[CH2:10][N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[CH:6][CH:7]=1.CCN(S(F)(F)[F:27])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:27][C@@H:11]1[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:12]1.[F:27][C@@H:11]1[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:12]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 66684241(4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

생성물 2

HCID 66684235(2R,4S)-tert-butyl 4-fluoro-2-(3-fluorophenyl)pyrrolidine-1-carboxylateHCID 66685044(2S,4S)-tert-butyl 4-fluoro-2-(3-fluorophenyl)pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of (4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate (I-4) (2.7 g, 9.6 mmol) in DCM (25 mL) in a plastic bottle at −78° C. was added DAST (2.5 mL, 19.2 mmol). The mixture was stirred at −78° C. for 2 hours and then was warmed slowly to room temperature overnight. The mixture was added drop wise to aqueous NaHCO3 at 0° C. and was extracted with DCM. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated. The two diasteromers were separated by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield (2R,4S)-tert-butyl 4-fluoro-2-(3-fluorophenyl)pyrrolidine-1-carboxylate (I-5A) (first eluting compound) and (2S,4S)-tert-butyl 4-fluoro-2-(3-fluorophenyl)pyrrolidine-1-carboxylate (I-5B). 1H NMR (400 MHz, CDCl3) δ 7.21 (dd, J=6.0, 6.0 Hz, 1 H), 6.92 (bd, J=8.0 Hz, 1 H), 6.88-6.82 (m, 2 H), 5.20 (bd, J=52.0 Hz, 1 H), 4.80 (bs, 1 H), 4.02 (dd, J=13.6, 22.8 Hz, 1 H), 3.65 (dd, J=12.8, 38.4 Hz, 1 H), 2.67-2.56 (m, 1 H), 1.89 (dt, J=11.2, 42 Hz, 1 H), 1.09 (s, 6 H). MS m/z 284.1 (M+1)+.

후처리

  1. temperaturewas warmed slowly to room temperature overnight
  2. extractionwas extracted with DCM
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe two diasteromers were separated by column chromatography on silica gel with EtOAc/hexanes gradient as eluant

출처 및 근거

ORD 기록
ord-09981be5a5664b31b744e2001bd9a836
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102671B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트