Hydrochloric Acid → HCID 11068249、化合物

HRID 1636595ノート

反応式

HRID 1636595 の反応式
[CH2:1]([C:4]1[C:5]([OH:21])=[C:6]([Br:20])[CH:7]=[C:8]2[C:12]=1[C@H:11]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:2]=C.[O:22]=[O+][O-].[BH4-].[Na+].Cl>CO>[Br:20][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([CH2:1][CH2:2][OH:22])[C:5]=1[OH:21])[C@H:11]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:10][CH2:9]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 10861106(S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-YL]ethyl]propanamide

生成物 1

HCID 11068249HCID 11068249、化合物収率 99%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of (S)-N-[2-(7-allyl-5-bromo-6-hydroxyindan-1-yl)ethyl]propionamide (588 mg, 1.67 mmol.) in methanol (30 mL) was cooled to about -70° C., to which was introduced ozone for 5 minutes. After confirming the disappearance of the starting material, an excess amount of powdery sodium borohydride (510 mg, 13.4 mmol.) was added to reaction mixture at about -70° C. to decompose ozonide. The reaction mixture was warmed to room temperature, which was neutralized with dilute hydrochloric acid, followed by extracting the organic matter with a mixture of ethyl acetate:butanol=1:1. The extract solution was dried over anhydrous magnesium sulfate, from which the solvent was distilled off under reduced pressure. The residue was then washed with diethyl ether to afford the title compound (yield 0.59 g, 99%).

後処理

  1. extractionby extracting the organic matter
  2. additionwith a mixture of ethyl acetate
  3. dry with materialThe extract solution was dried over anhydrous magnesium sulfate, from which the solvent
  4. distillationwas distilled off under reduced pressure
  5. washThe residue was then washed with diethyl ether

出典と根拠

ORDレコード
ord-5c8b0d644b5348cf964e05124f820c60
出典データセット
uspto-grants-2000_03
特許番号
US06034239

反応ノート

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