Pyridine → HCID 3352947, compound

HRID 394793Notes

Reaction equation

HRID 394793 reaction equation
[C:1]([CH:5]1[CH2:9][CH2:8][CH2:7][NH:6]1)([O:3][CH3:4])=[O:2].N1C=CC=CC=1.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>C(Cl)Cl>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([N:6]2[CH2:7][CH2:8][CH2:9][CH:5]2[C:1]([O:3][CH3:4])=[O:2])=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 94239Methyl DL-prolinate

Product 1

HCID 3352947HCID 3352947, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-carbomethoxypyrrolidine (d,1-proline methylester, 1.64 g, 12.7 mmol) with pyridine (10.1 g, 12.7 mmol) in CH2Cl2 (100 mL) at 0° C. was added 4-nitrobenzoyl chloride (2.36 g, 12.7 mmol) in CH2Cl2 (25 mL) dropwise. The reaction was allowed to warm to ambient temperature and stirred 18 h. The reaction was evaporated and applied to a silica gel flash column and eluted with a gradient of 2:1 Hexane:EtOAc to 1:2 Hexane:EtOAc. There was isolated 1.3 g of the title compound; LRMS (M+H)+ m/z=279.

Workup

  1. customThe reaction was evaporated
  2. washeluted with a gradient of 2:1 Hexane

Sources & evidence

ORD record
ord-9bd0a5569f254d2fa5701dd55d26b0e0
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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