Diethylamine → HCID 178478031, compound

HRID 81390Notes

Reaction equation

HRID 81390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]1[N:23]=[CH:22][N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][NH:19]2.C(NCC)C>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]1[N:23]=[CH:22][N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][NH:19]2

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 178478029HCID 178478029, compound

Product 1

HCID 178478031HCID 178478031, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

110 mg of the racemate 6-{-2-[2-(2-chlorophenyl)ethyl]pyrrolidin-1-yl}-9H-purine are dissolved in 7 ml of methanol and 2 ml of diethylamine and divided into 9 vials. The solutions are separated by means of supercritical CO2 (SFC) on Chiralcel OD-H using 5 ml/min of CO2+40% of MOH0, 5 DEA, giving 46.6 mg of 6-{(R)-2-[2-(2-chlorophenyl)ethyl]pyrrolidin-1-yl}-9H-purine (“A5b”) having an enantiomer ratio of 98.8%:1.2%.

Workup

  1. customThe solutions are separated by means of supercritical CO2 (SFC) on Chiralcel OD-H

Sources & evidence

ORD record
ord-556f408eb8994c1fad28c50d95384f33
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Reaction notes

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