2,3-Dichloro-alpha-methylbenzylamine → HCID 53748281、化合物

HRID 1599217ノート

反応式

HRID 1599217 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([NH2:11])[CH3:10].C(O)(=O)[C@H](C1C=CC=CC=1)O.[OH-].[Na+]>C(OC)(C)(C)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]([NH2:11])[CH3:10]

参加物

5

反応物 3

HCID 12152,3-Dichloro-alpha-methylbenzylamineHCID 14798Sodium HydroxideHCID 439616(S)-mandelic acid

生成物 1

HCID 53748281HCID 53748281、化合物収率 40%

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒2 回

反応条件

温度
45 °C

実験手順

A solution consisting of 10 g of (RS)-1-(2,3-dichlorophenyl)ethylamine and 30 g of methyl t-butyl ether was heated to 45° C. while stirring, and a mixture of 3.6 g of L-mandelic acid and 30 g of methyl t-butyl ether was added thereto over about 30 minutes, followed by stirring at the see temperature for 30 minutes. Then, after cooled to 20° C. over 6 hours, the precipitated crystals were filtered, washed twice with 20 g of methyl t-butyl ether and dried to obtain 7.2 g of diastereomer salt. 21 g of a 5% aqueous sodium hydroxide solution was added to the crystals, followed by extraction twice with 10 g of methyl t-butyl ether. The solvent was distilled off from the resulting organic layer to obtain 4 g of (R)-1-(2,3-dichlorophenyl)ethylamine. This had the optical purity of 90.4%ee.

後処理

  1. additionwas added
  2. stirringby stirring at the see temperature for 30 minutes
  3. temperatureThen, after cooled to 20° C. over 6 hours
  4. filtrationthe precipitated crystals were filtered
  5. washwashed twice with 20 g of methyl t-butyl ether
  6. customdried
  7. customto obtain 7.2 g of diastereomer salt
  8. extractionfollowed by extraction twice with 10 g of methyl t-butyl ether
  9. distillationThe solvent was distilled off from the resulting organic layer

出典と根拠

ORDレコード
ord-28b4781c411f4570adab9129dd8cfae1
出典データセット
uspto-grants-1998_04
特許番号
US05739401

反応ノート

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