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

HRID 1727190

反応式

HRID 1727190 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 30318Osmium Tetroxide触媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-77aa9fbaf587432baea86712004ca9a5
出典データセット
uspto-grants-2009_02
特許番号
US07494992B2

関連ノート

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