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Sodium Hydroxide → (R)-1-(3,4-dichlorophenyl)ethanamine

HRID 1599216
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HRID 1599216 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH2:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(=O)[C@H](C1C=CC=CC=1)O.[OH-].[Na+]>C(OC)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH2:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 439616(S)-mandelic acidHCID 31592421-(3,4-Dichlorophenyl)ethanamine

생성물 1

HCID 793515(R)-1-(3,4-dichlorophenyl)ethanamine수율 44.4%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매2회

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온도
45 °C

실험 절차

A solution consisting of 41 g of (RS)-1-(3,4-dichlorophenyl)ethylamine and 78 g of methyl t-butyl ether was heated to 45° C. while stirring, and a mixture of 14.6 g of L-mandelic acid and 90 g of methyl t-butyl ether was added thereto over about 30 minutes, followed by stirring at the same temperature for 30 minutes. Then, after cooled to 20° C. over 6 hours, the precipitated crystals were filtered, washed twice with 40 g of methyl t-butyl ether and dried to obtain 32.9 g of diastereomer salt. 82 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 18.2 g of (R)-1-(3,4-dichlorophenyl)ethylamine. This had the optical purity of 87.4%ee.

후처리

  1. additionwas added
  2. stirringby stirring at the same temperature for 30 minutes
  3. temperatureThen, after cooled to 20° C. over 6 hours
  4. filtrationthe precipitated crystals were filtered
  5. washwashed twice with 40 g of methyl t-butyl ether
  6. customdried
  7. customto obtain 32.9 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

출처 및 근거

ORD 기록
ord-5e99564cfad84e268d9a7d29d9c18dde
출처 데이터셋
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05739401

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