4-Chlorophenyl Isocyanate → HCID 66758335, compound

HRID 557052Notes

Reaction equation

HRID 557052 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:14][CH3:15])[C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=2)=[O:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 20800658Tert-butyl 3-(ethylamino)pyrrolidine-1-carboxylate

Product 1

HCID 66758335HCID 66758335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-ethylamino-pyrrolidine-1-carboxylic acid tert-butyl ester (0.33 g, 1.5 mmol) in DMF (5.0 mL) was added drop wise a solution of 4-chlorophenyl isocyanate (0.23 g, 1.51 mmol) in DMF (2.5 mL) at room temperature and the resulting mixture was stirred for 3 h. The reaction mixture was concentrated in vacuo and the crude product was purified on silica using hexane/ethyl acetate (50%) followed by ethyl acetate (100%) to give the desired product as white foamy solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified on silica

Sources & evidence

ORD record
ord-7a7bf69d523841e7b51c91e2a2ea92d6
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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