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N-cyclopropylmethylphthalimide → 3-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one

HRID 733220
ノート
印刷プレビュー

反応式

HRID 733220 の反応式
[CH:1]1([CH2:4][N:5]2[C:9](=[O:10])[C:8]3=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]3[C:6]2=[O:15])[CH2:3][CH2:2]1>CO.[BH4-].[K+].ClCCl>[OH:10][CH:9]1[C:8]2[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6](=[O:15])[N:5]1[CH2:4][CH:1]1[CH2:2][CH2:3]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 4121050N-cyclopropylmethylphthalimide

生成物 1

HCID 179664273-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one収率 94.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 4192641Potassium borohydride溶媒

反応条件

温度
20 °C

実験手順

3-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 4.3 g of N-cyclopropylmethylphthalimide in 40 cm3 of methanol and 1.2 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the region of 0° C. and distilled water is added dropwise. The precipitate obtained is filtered off and the solid obtained is then taken up in dichloromethane and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 4.1 g of 3-hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white powder (Rf=0.38, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

後処理

  1. custom3-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one is prepared
  2. temperatureis then cooled to a temperature in the region of 0° C.
  3. distillationdistilled water
  4. additionis added dropwise
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. customthe solid obtained
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

出典と根拠

ORDレコード
ord-f84d6a7e6f444fe1a447af059b864f19
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07589117B2

反応ノート

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