4-Iodobenzyl alcohol → 2-{4-[3-(4-Hydroxymethyl-phenyl)-prop-2-ynyloxy]-phenoxymethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 12927

Reaction equation

HRID 12927 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[CH:24])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:26]1[CH:33]=[CH:32][C:29]([CH2:30][OH:31])=[CH:28][CH:27]=1.N1CCCC1>Cl[Pd]Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[C:24][C:26]2[CH:33]=[CH:32][C:29]([CH2:30][OH:31])=[CH:28][CH:27]=2)=[CH:17][CH:16]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 290124-Iodobenzyl alcoholHCID 31268PyrrolidineHCID 866196562-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 684297222-{4-[3-(4-Hydroxymethyl-phenyl)-prop-2-ynyloxy]-phenoxymethyl}-pyrrolidine-1-carboxylic acid tert-butyl esterYield 20.5%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

General procedure A was followed using the product from step 3 Example 1 (266 mg, 1.0546 mmol), p-iodobenzylalcohol (156.5 mg, 0.669 mmol), PdCl2 (2.5 mg, 0.014 mmol), pyrrolidine (0.277 mL, 3.34 mmol), water (0.844 mL) to give the title compound (60 mg, 20.5%).

Sources & evidence

ORD record
ord-98f3564561be419fbc072cf9e881ed13
Source dataset
uspto-grants-2010_06
Patent number
US07728032B2

Linked notes

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