1-Chloroethyl chloroformate → 3-(3-Chloro-5-fluorophenyl)-3-methoxypyrrolidine

HRID 575963Notes

Reaction equation

HRID 575963 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]([Cl:22])[CH:16]=2)([O:13][CH3:14])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[Cl: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

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 674034071-Benzyl-3-(3-chloro-5-fluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 462192233-(3-Chloro-5-fluorophenyl)-3-methoxypyrrolidineYield 52%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Preparation according to Example 1: (−)-1-benzyl-3-(3-chloro-5-fluorophenyl)-3-methoxypyrrolidine (0.265 g, 0.83 mmol), 1,2-dichloroethane (20 ml), 1-chloroethyl chloroformate (0.47 g, 3.31 mmol). Purification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50) gave the title compound 0.099 g (52%). [a]D=−2.8° (methanol). MS m/z (relative intensity, 70 eV) 229 (M+, 1), 214 (53), 199 (bp), 187 (81), 133 (56).

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-0eec7eda9a394c7e8f13e574baf8bb3f
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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