2-Chlorobenzoic Acid → HCID 28345633, compound

HRID 1784350Notes

Reaction equation

HRID 1784350 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[CH2:28][OH:29]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[CH2:28][OH:29])=[O:6]

Participants

5

Reactant 3

HCID 83742-Chlorobenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 640091L-Prolinol

Product 1

HCID 28345633HCID 28345633, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-chlorobenzoic acid (10 g; 63.9 mmol) in dimethylformamide (100 ml) under nitrogen was added carbonyldiimidazole (10.9 g; 67.1 mmol) and the solution stirred for 1 h at room temperature. (S)-(+)-2-pyrrolidinemethanol (7.56 ml, 76.6 mmol) was added and the mixture stirred at 40° C. for 18 h. The solvent was removed under reduced pressure and the crude product purified by chromatography on silica (eluting with 50% to 75% ethyl acetate in heptane) to afford (S)-1-(2-chlorobenzoyl)-2-pyrrolidinemethanol (10.2 g), which was used directly in the next step.

Workup

  1. stirringthe mixture stirred at 40° C. for 18 h
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product purified by chromatography on silica (eluting with 50% to 75% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6cefee6797af4be89e1c69eee56f99c0
Source dataset
uspto-grants-2009_03
Patent number
US07504390B2

Reaction notes

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