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Sodium Chloride → (R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20397
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HRID 20397 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH:14]=[O:15])[CH2:12][O:11][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]1[CH:34]=[C:33]([CH2:35][CH2:36][N+:37]([O-:39])=[O:38])[CH:32]=[C:31]([F:40])[CH:30]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:15])[C@@H:36]([N+:37]([O-:39])=[O:38])[CH2:35][C:33]2[CH:34]=[C:29]([F:28])[CH:30]=[C:31]([F:40])[CH:32]=2)[CH2:12][O:11][C:10]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 552507531,3-Difluoro-5-(2-nitroethyl)benzeneHCID 86615365(R)-5-Formyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

생성물 1

HCID 68563474(R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To (R)-5-formyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester (1.03 g, 2.80 mmol) and 1,3-difluoro-5-(2-nitroethyl)-benzene (0.577 g, 3.08 mmol) in tetrahydrofuran (5 mL) at −0° C. under nitrogen add tetrabutylammonium fluoride (3 mL, 3.0 mmol, 1.0 M in tetrahydrofuran). Stir 20 minutes and add half saturated aqueous sodium chloride (20 mL) and ethyl acetate (100 mL). Separate the layers and wash the organic layer with water and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Purify on silica gel, eluting with 0:100 to 50:50 ethyl acetate:hexanes, then re-crystallize from hexanes/dichloromethane to give the desired compound.

후처리

  1. customSeparate the layers
  2. washwash the organic layer with water and saturated aqueous sodium chloride
  3. dry with materialDry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify on silica gel
  7. washeluting with 0:100 to 50:50 ethyl acetate
  8. customhexanes, then re-crystallize from hexanes/dichloromethane

출처 및 근거

ORD 기록
ord-1469cfe8cdfc4662ac59cec026fa47d2
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745438B2

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