Acetone → 3-Benzyldecahydro-1,5-methanocyclopenta[d]azepine-6,7-diol

HRID 1727190

반응식

HRID 1727190 반응식
[C:1]1([CH2:7][N:8]2[CH2:17][CH:16]3[CH2:18][CH:10]([CH:11]4C3C=C[CH2:12]4)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:23]CC1.[O-][Si]([O-])=O.[Mg+2].S([O-])(O)=O.[Na+].[CH3:37][C:38]([CH3:40])=[O:39]>[Os](=O)(=O)(=O)=O>[C:1]1([CH2:7][N:8]2[CH2:17][CH:16]3[CH2:18][CH:10]([CH:11]4[CH:40]3[CH:38]([OH:39])[CH:37]([OH:23])[CH2:12]4)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 180AcetoneHCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 598378489-Benzyl-9-aza-tricyclo[5.3.1.02,6]undec-3-ene

생성물 1

HCID 598378623-Benzyldecahydro-1,5-methanocyclopenta[d]azepine-6,7-diol수율 80%

시약·촉매·용매 1

HCID 30318Osmium Tetroxide촉매

실험 절차

A solution of 9-(phenylmethyl)-9-azatricyclo[5.3.1.02,6]undec-3-ene (Preparation 35, 6.7 g, 28.0 mmol), N-methylmorpholine N-oxide (3.45 g, 29.45 mmol) and osmium tetroxide (2.5 wt % in 2-methyl-2-propanol, 2 □l) in acetone (50 ml) was stirred for 18 h. Florisil and aqueous sodium hydrogensulfite (4 ml) were added and the reaction mixture was stirred for 30 min and filtered. Methanol (50 ml) was added and the reaction mixture was concentrated to give an oil which was purified by flash chromatography eluting with ethyl acetate:hexane (50:50) to give an oil (6.2 g, 80%) which crystallises upon standing.

후처리

  1. filtrationfiltered
  2. additionMethanol (50 ml) was added
  3. concentrationthe reaction mixture was concentrated
  4. customto give an oil which
  5. customwas purified by flash chromatography
  6. washeluting with ethyl acetate:hexane (50:50)

출처 및 근거

ORD 기록
ord-77aa9fbaf587432baea86712004ca9a5
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07494992B2

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