Triethylamine → ethyl 3-[4-cyano-(2R)-2-(1-t-butoxycarbonylpyrrolidine-2-ylmethoxy)phenyl]acrylate

HRID 2187944Notes

Reaction equation

I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH:25]=[CH2:26].C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH:26]=[CH:25][C:24]([O:28][CH2:29][CH3:30])=[O:27])=[C:3]([O:10][CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:4]=1)#[N:7]

Participants

Conditions

Temperature: 100 °C

Procedure

3.7 g (8.6 mmol) of 4-iodo-3-[(2R)-(1-t-butoxycarbonyl-pyrrolidine-2-ylmethoxy)]benzonitrile was dissolved in 40 ml of DMF. 4.68 ml (43 mmol) of ethyl acrylate, 6.1 ml (43 mmol) of triethylamine and 194 mg (0.85 mmol) of palladium acetate were added to the obtained solution, and they were stirred at 100° C. overnight. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product was treated with ethyl acetate as the extraction solvent in an ordinary manner to obtain the crude product, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

customto obtain the crude product, which
customwas purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-88d33be5519c4cffa76c55493af45a33
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410538B2

Reaction notes

Loading…