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

HRID 1015520ノート

反応式

HRID 1015520 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7e63bac8c780440699f0c72047efd063
出典データセット
uspto-grants-2011_07
特許番号
US07985759B2

反応ノート

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