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tert-Butanol → (6S)-4-benzyl-6-(4-fluorophenyl)morpholin-3-one

HRID 880230
ノート
印刷プレビュー

反応式

HRID 880230 の反応式
[CH2:1]([N:8]([CH2:13][C@H:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[OH:15])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)(C)C.CC(C)([O-])C.[K+].[Cl-].[NH4+]>O>[CH2:1]([N:8]1[CH2:13][C@H:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:15][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67352707(1S)-1-(4-fluorophenyl)-2-(N-benzyl-N-chloroacetylamino)ethanol

生成物 1

HCID 15982164(6S)-4-benzyl-6-(4-fluorophenyl)morpholin-3-one収率 98%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
22 °C

実験手順

Add N-benzyl-2-chloro-N-[(2S)-2-(4-fluorophenyl)-2-hydroxyethyl]acetamide (1440 g, 4.48 mol) to tert-butyl alcohol (14.5 L) and add potassium tert-butoxide (753 g, 6.73 mol) portion-wise while maintaining the mixture at 22° C. Maintain the mixture at 22° C. and stir for 1.5 hours. Add a saturated aqueous solution of ammonium chloride (1306 g) to quench the reaction. Stir for an additional 1 hour and then add H2O (2 L). Extract with EtOAc (2×10 L); combine the extracts; and concentrate the extracts under reduced pressure provide a residue. Re-dissolve the residue in EtOAc (20 L) and wash with H2O (10 L). Dry the EtOAc solution over Na2SO4 and filter. Collect the filtrate and remove the solvent under reduced pressure to provide the title compound as a colorless oil (1250 g, 98%). MS (m/z): 286 (M+1).

後処理

  1. temperatureMaintain the mixture at 22° C.
  2. customto quench
  3. customthe reaction
  4. stirringStir for an additional 1 hour
  5. extractionExtract with EtOAc (2×10 L)
  6. concentrationand concentrate the extracts under reduced pressure
  7. customprovide a residue
  8. washRe-dissolve the residue in EtOAc (20 L) and wash with H2O (10 L)
  9. dry with materialDry the EtOAc solution over Na2SO4
  10. filtrationfilter
  11. customCollect the filtrate
  12. customremove the solvent under reduced pressure

出典と根拠

ORDレコード
ord-ebe9a2bbf1814144a7e66b2ea828d937
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993568B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート