Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 1,1-Dimethylethyl (4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetate

HRID 893508ノート

反応式

HRID 893508 の反応式
[C:1]([CH2:3][CH:4]([OH:16])[CH2:5][CH:6]([OH:15])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])#[N:2].[C:17]12(CS(O)(=O)=O)C(C)(C)C(C[CH2:23]1)C[C:18]2=O>COC(OC)(C)C>[C:1]([CH2:3][C@H:4]1[O:16][C:17]([CH3:23])([CH3:18])[O:15][C@@H:6]([CH2:7][C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:5]1)#[N:2]

参加物

4

反応物 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 222829971,1-Dimethylethyl 6-cyano-3,5-dihydroxyhexanoate

生成物 1

HCID 27342871,1-Dimethylethyl (4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetate

試薬・触媒・溶媒 1

HCID 64952,2-Dimethoxypropane溶媒

実験手順

Crude [R-(R*,R*)]-1,1-dimethylethyl 6-cyano-3,5-dihydroxyhexanoate, 15 g (61 mol), is dissolved in 150 mL of 2,2-dimethoxypropane, camphorsulfonic acid is added, and the solution is stirred for 18 hours at room temperature. Concentration and flash chromatography after concentration in vacuo provides 11.8 g of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate as an off-white solid, mp 64.7°-68° C. with acceptable IR, NMR, C-NMR and analysis.

後処理

  1. concentrationConcentration and flash chromatography
  2. concentrationafter concentration in vacuo

出典と根拠

ORDレコード
ord-8f9fbad77132459c8b1c1f3a13ed9770
出典データセット
uspto-grants-1992_06
特許番号
US05124482

反応ノート

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