Sodium hydride → tert-butyl (S)-3-(2-bromo-5-fluorobenzyloxy)pyrrolidine-1-carboxylate

HRID 928070ノート

反応式

HRID 928070 の反応式
[H-].[Na+].[OH:3][C@H:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1.[Br:16][C:17]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:18]=1[CH2:19]Br>C1COCC1>[Br:16][C:17]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:18]=1[CH2:19][O:3][C@H:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzeneHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

生成物 1

HCID 68923111tert-butyl (S)-3-(2-bromo-5-fluorobenzyloxy)pyrrolidine-1-carboxylate収率 100.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60% oil dispersion, 0.24 g) was added to a stirred solution of tert-butyl (S)-3-hydroxypyrrolidine-1-carboxylate (0.935 g) in THF (15 mL) and the mixture was stirred for 5 minutes. 2-Bromo-5-fluorobenzyl bromide (1.608 g) was added and stirring was continued for 20 hours. The resultant suspension was filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-15% to give tert-butyl (S)-3-(2-bromo-5-fluorobenzyloxy)-pyrrolidine-1-carboxylate (1.88 g) as a colourless oil.

後処理

  1. stirringstirring
  2. waitwas continued for 20 hours
  3. filtrationThe resultant suspension was filtered
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-15%

出典と根拠

ORDレコード
ord-fc74d8ab5ee94ea7b305504110d3b307
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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