1,2-Dichloroethane → 3-(3,5-Difluorophenyl)-3-methoxypyrrolidine

HRID 1188159Notes

Reaction equation

HRID 1188159 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)([O:13][CH3:14])[CH2:9]1)C1C=CC=CC=1.ClCCCl.ClC(OC(Cl)C)=O>CO>[F:22][C:17]1[CH:16]=[C:15]([C:10]2([O:13][CH3:14])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:20]=[C:19]([F:21])[CH:18]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5213051-Chloroethyl chloroformateHCID 199358491-Benzyl-3-(3,5-difluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 199358743-(3,5-Difluorophenyl)-3-methoxypyrrolidineYield 35.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Preparation according to Example 1. (+)-1-benzyl-3-(3,5-difluorophenyl)-3-methoxypyrrolidine (0.35 g, 1.15 mmol), 1,2-dichloroethane (20 ml), 1-chloroethyl chloroformate (0.50 ml, 4.6 mmol) refluxed for 2 h, and methanol (10 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 (0.087 g, 35%). [a]D=+2.1° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 185-187° C. MS m/z (rel. intensity, 70 eV) 213 (M+, 1), 198 (54), 183 (bp), 171 (85), 141 (47).

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-f027db752f20417e90ccae3395ff9715
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

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