(R)-(+)-3-Chlorostyrene oxide → HCID 68901479, compound

HRID 1985025Notes

Reaction equation

HRID 1985025 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH2:14])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C@H:19]1[O:21][CH2:20]1>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:17]=[C:18]([C@@H:19]([OH:21])[CH2:20][NH:14][C@@H:10]2[CH2:11][CH2:12][CH2:13][C@@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=3)[CH2:9]2)[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 54402266HCID 54402266, compound

Product 1

HCID 68901479HCID 68901479, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10 ml of toluene, 1.92 g of (1R,3R)-3-(3-hydroxyphenyl)cyclohexylamine and 1.55 g of (R)-3-chlorostyrene oxide was heated under reflux for 4 hours. The reaction liquid was cooled to room temperature, a seed crystal was inoculated into it, and stirred as such for 30 minutes. The precipitated crystal was taken out through filtration, and then dried under aeration at 50° C. for 2.5 hours to obtain 2.42 g of the entitled compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customThe reaction liquid
  4. filtrationThe precipitated crystal was taken out through filtration
  5. customdried under aeration at 50° C. for 2.5 hours

Sources & evidence

ORD record
ord-c0f6eb70a5d54245a5cfc8f20266af02
Source dataset
uspto-grants-2009_06
Patent number
US07544841B2

Reaction notes

Loading…