(Diethylamino)sulfur trifluoride → (2S,4S)-1-Tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

HRID 1015520노트

반응식

HRID 1015520 반응식
O[C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.C(N(S(F)(F)[F:24])CC)C.C([O-])(O)=O.[Na+]>ClCCCl>[F:24][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1

참가 물질

5

반응물 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

생성물 1

HCID 10977773(2S,4S)-1-Tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate수율 100%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a stirred solution of compound obtained in step II (24.5 g, 0.1 mol) in 1,2-dichloroethane (300 mL) cooled to −10° C. was added diethylaminosulfur trifluoride (19.7 mL, 0.15 mol) over a period of 30 minutes. The reaction mixture was stirred at this temperature for 1 h then at room temperature for 16 h. The reaction mixture was quenched by adding mixture of crushed ice (300 g) and solid NaHCO3 (25.2 g, 0.3 mol). The two layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure to obtain 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate as a viscous liquid (24.7 g) in 100% yield. [α]D −53.3, (c, 1.0, CHCl3). m/z (M+1) 248; 1H NMR (CDCl3) 300 MHz δ 5.20 (ddd, J=3.8, 3.8, 49.1 Hz, 1H), 4.55 (d, J=9.5 Hz, ½H), 4.42 (d, J=8.9 Hz, ½H), 3.90-3.55 (m, 2H), 3.75 (s, 3H), 2.55-2.20 (m, 2H), 1.46 (s, 3H), 1.41 (s, 6H).

후처리

  1. waitat room temperature for 16 h
  2. customThe reaction mixture was quenched
  3. additionby adding
  4. customThe two layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-7e63bac8c780440699f0c72047efd063
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985759B2

반응 노트

불러오는 중…