Pyrrolidine → HCID 86583564, compound

HRID 1016792Notes

Reaction equation

HRID 1016792 reaction equation
C(N(C(C)C)C(C)C)C.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH:24]([C:30]2[CH:35]=[C:34]([CH2:36]OS(C)(=O)=O)[CH:33]=[C:32]([O:42][CH2:43][CH3:44])[CH:31]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=1)#[N:16]>C1COCC1>[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH:24]([C:30]2[CH:35]=[C:34]([CH2:36][N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:33]=[C:32]([O:42][CH2:43][CH3:44])[CH:31]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=1)#[N:16]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 86583562HCID 86583562, compound

Product 1

HCID 86583564HCID 86583564, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Ethyldiisopropylamine (132 mg, 1.02 mmol) and pyrrolidine (145 mg, 2.04 mmol) were added to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-methanesulphonyloxymethyl-phenyl)-acetate (221 mg, 0.511 mmol) obtained in Example 234.3 in THF (2 ml) and the mixture was stirred for 1 h. at room temperature. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, CH2Cl2/MeOH 99:1). There were obtained 153 mg (73%) of ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-pyrrolidin-1-ylmethyl-phenyl)-acetate as a yellowish foam; MS: 408 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 99:1)

Sources & evidence

ORD record
ord-12d926c1073849019fc2eaca4dae1bb6
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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