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

HRID 880230
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인쇄 미리보기

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HRID 880230 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962
Water
용매

반응 조건

온도
22 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ebe9a2bbf1814144a7e66b2ea828d937
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08993568B2

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