Water → benzyl (3R,4R)-3-amino-4-fluoropyrrolidine-1-carboxylate

HRID 928194ノート

反応式

HRID 928194 の反応式
[N:1]([C@H:4]1[C@H:8]([F:9])[CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[NH2:1][C@H:4]1[C@H:8]([F:9])[CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1

参加物

5

反応物 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57970079Benzyl trans-3-azido-4-fluoro-pyrrolidine-1-carboxylate

生成物 1

HCID 57970069benzyl (3R,4R)-3-amino-4-fluoropyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (trans)-benzyl 3-azido-4-fluoropyrrolidine-1-carboxylate (30 g, 0.114 mol) in THF (0.3 L) was added PPh3 (33 g, 0.126 mol) portion wise at 0-5° C. The resulting mixture was then warmed to rt and stirred for 2 hr. 30 mL of water was then added and the resulting mixture was heated to reflux overnight. The reaction mixture was concentrated and the residue diluted with EtOAc (0.2 L) and extracted with sat. citric acid (4×100 mL). The combined aqueous extracts were washed with EtOAc (3×50 mL), then adjusted pH to 8 with sat. aq. K2CO3, and extracted with DCM (4×100 mL). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4, concentrated, then dried in vacuo to give the title compound as light yellow oil that solidified on standing to afford an off-white solid (16 g, 59% yield).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue diluted with EtOAc (0.2 L)
  5. extractionextracted with sat. citric acid (4×100 mL)
  6. washThe combined aqueous extracts were washed with EtOAc (3×50 mL)
  7. extractionextracted with DCM (4×100 mL)
  8. washThe combined organic extracts were washed with brine (100 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-65c69b2219ed4c899863f0410ec0db27
出典データセット
uspto-grants-2016_03
特許番号
US09290496B2

反応ノート

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