Tert-butyl 2-(4-aminophenyl)pyrrolidine-1-carboxylate → 4-(2-Ethoxymethyl-pyrrolidin-1-ylmethyl)-phenylamine

HRID 2236509Notes

Reaction equation

HRID 2236509 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)=O)(C)(C)C.BrC1C=CC(CN2CCC[CH:27]2[CH2:31][O:32][CH2:33]C)=CC=1>>[CH2:31]([O:32][CH2:33][CH:6]1[CH2:10][CH2:11][CH2:12][N:8]1[CH2:9][C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=1)[CH3:27]

Participants

3

Reactant 2

HCID 44607625Tert-butyl 2-(4-aminophenyl)pyrrolidine-1-carboxylateHCID 686929221-(4-Bromo-benzyl)-2-ethoxymethyl-pyrrolidine

Product 1

HCID 686942984-(2-Ethoxymethyl-pyrrolidin-1-ylmethyl)-phenylamineYield 47%

Procedure

Using the same procedure described for the preparation of 2-(4-Amino-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, the title compound is prepared from 1-(4-Bromo-benzyl)-2-ethoxymethyl-pyrrolidine (using the crude product obtained in the previous step) in 47% yield (two steps, based on crude residue, ˜85%).

Workup

  1. customobtained in the previous step) in 47% yield (two steps, based on crude residue, ˜85%)

Sources & evidence

ORD record
ord-e08ff7ec9e804fe483703b357f3f5583
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…