Thionyl Chloride → Benzyl 2-(4-(chlorocarbonyl)-3-fluorophenyl)pyrrolidine-1-carboxylate

HRID 415156Notes

Reaction equation

HRID 415156 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[C:18]([F:25])[CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:28])=O>ClCCl>[Cl:28][C:20]([C:19]1[CH:23]=[CH:24][C:16]([CH:12]2[CH2:13][CH2:14][CH2:15][N:11]2[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[CH:17][C:18]=1[F:25])=[O:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 666213044-(1-(Benzyloxycarbonyl)pyrrolidin-2-yl)-2-fluorobenzoic acid

Product 1

HCID 86633086Benzyl 2-(4-(chlorocarbonyl)-3-fluorophenyl)pyrrolidine-1-carboxylateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)-2-fluorobenzoic acid (8.4 g, 24.5 mmol) in anhydrous dichloromethane (300 mL) was added dropwise thionyl chloride (2.2 mL, 29.4 mmol) at 0° C. After the addition, the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo to give benzyl 2-(4-(chlorocarbonyl)-3-fluorophenyl)pyrrolidine-1-carboxylate (8.87 g).

Workup

  1. additionAfter the addition
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8f7b02b5e249469ead070e44813ebc81
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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