1,2-Dichloroethane → HCID 46196348, compound

HRID 1188152Notes

Reaction equation

HRID 1188152 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[F:22])([O:13][CH3:14])[CH2:9]1)C1C=CC=CC=1.ClCCCl.ClC(OC(Cl)C)=O>CO>[Cl:21][C:17]1[C:16]([F:22])=[C:15]([C:10]2([O:13][CH3:14])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5213051-Chloroethyl chloroformateHCID 67402567HCID 67402567, compound

Product 1

HCID 46196348HCID 46196348, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Preparation according to Example 1. (−)-1-benzyl-3-(3-chloro-2-fluorophenyl)-3-methoxypyrrolidine (0.82 g, 2.56 mmol), 1,2-dichloroethane (10 ml), 1-chloroethyl chloroformate (1.12 ml, 10.25 mmol) refluxed for 2 h, and methanol (20 ml) reflux 1 h. Purification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50) gave the title compound (0.38 g, 65%). [a]D=−7.1° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 183-185° C. MS m/z (rel. intensity, 70 eV) 229 (M+, 1), 199 (87), 187 (bp), 157 (55), 133 (51).

Workup

  1. customPreparation
  2. customPurification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50)

Sources & evidence

ORD record
ord-e1d069491aee4482a6470452c7f1b411
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

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