1-(4-Iodophenyl)-1H-Pyrazole → (r)-2-[4-(4-Pyrazol-1-yl-phenoxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 750071Notes

Reaction equation

HRID 750071 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH:33]=[CH:32][CH:31]=[N:30]2)=[CH:25][CH:24]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:23]2[CH:24]=[CH:25][C:26]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)=[CH:27][CH:28]=2)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 27764811-(4-Iodophenyl)-1H-PyrazoleHCID 68999591(R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68998060(r)-2-[4-(4-Pyrazol-1-yl-phenoxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 64.3%

Procedure

Followed the same procedure as that of step 1 in Example 133 with the use of (R)-2-(4-hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (147 mg, 0.5 mmol) and 1-(4-iodo-phenyl)-1H-pyrazole (203 mg, 0.75 mmol) to afford the title product (140 mg, 60% yield).

Sources & evidence

ORD record
ord-5bc499c24a1841beac817ccdf2115786
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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