1-Chloroethyl chloroformate → 3-(3-Chloro-4-fluorophenyl)-3-methoxypyrrolidine

HRID 575964Notes

Reaction equation

HRID 575964 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[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]=[CH:19][C:18]=1[F:21]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 674012051-Benzyl-3-(3-chloro-4-fluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 462193563-(3-Chloro-4-fluorophenyl)-3-methoxypyrrolidineYield 51.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Preparation according to Example 1: (+)-1-benzyl-3-(3-chloro-4-fluorophenyl)-3-methoxypyrrolidine (0.405 g, 1.27 mmol), 1,2-dichloroethane (20 ml), 1-chloroethyl chloroformate (0.72 g, 5.06 mmol). Purification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50) gave the title compound 0.15 g (51%). [a]D=+3.3° (methanol). MS m/z (relative intensity, 70 eV) 229 (M+, 1), 214 (37), 199 (77), 187 (bp), 157 (38).

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-a536a07beef348c5a474565585b7c4cb
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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