(3RS,4RS)-3-(1-ethoxycarbonylmethyl-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester → (3RS,4RS)-[7-(4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl)-3,4-dihydro-2H-quinolin-1-yl]-acetic acid ethyl ester

HRID 1531484Notes

Reaction equation

HRID 1531484 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[CH:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:38][CH:37]=2)[CH2:9]1)=O)(C)(C)C>ClC(Cl)C.[Br-].[Zn+2].[Br-]>[CH2:50]([O:49][C:47](=[O:48])[CH2:46][N:43]1[C:44]2[C:39](=[CH:38][CH:37]=[C:36]([CH2:35][O:34][CH:10]3[CH:11]([C:14]4[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[O:32][CH3:33])=[CH:18][CH:19]=4)[CH2:12][CH2:13][NH:8][CH2:9]3)[CH:45]=2)[CH2:40][CH2:41][CH2:42]1)[CH3:51]

Participants

4

Reactant 1

HCID 69486566(3RS,4RS)-3-(1-ethoxycarbonylmethyl-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69486004(3RS,4RS)-[7-(4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl)-3,4-dihydro-2H-quinolin-1-yl]-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

In analogy to the procedure described in example 1(e), the (3RS,4RS)-3-(1-ethoxycarbonylmethyl-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester was deprotected with zinc bromide in dichloroethane to yield the (3RS,4RS)-[7-(4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl)-3,4-dihydro-2H-quinolin-1-yl]-acetic acid ethyl ester as a yellow oil; MS: 603 (M+H)+.

Sources & evidence

ORD record
ord-4d47f6e8c7614ac6963d79a9b24e0078
Source dataset
uspto-grants-2001_03
Patent number
US06197959B1

Reaction notes

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