Methyl 3-(bromomethyl)benzoate → 3-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid methyl ester

HRID 222685Notes

Reaction equation

HRID 222685 reaction equation
C(O[C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[CH:24]=1.C(OC(N1CC[C:43]2C=C(OCC3C=CC(C(OC)=O)=CC=3)C=C[C:42]=2[CH2:41][CH2:40]1)=O)(C)(C)C.COC(=O)C1C=CC(COC2C=CC3CNCCCC=3C=2)=CC=1>>[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][O:19][C:16]2[CH:17]=[CH:18][C:11]3[CH2:10][CH2:9][N:8]([CH:6]4[CH2:43][CH2:42][CH2:41][CH2:40]4)[CH2:14][CH2:13][C:12]=3[CH:15]=2)[CH:24]=1

Participants

5

Reactant 4

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 18173274tert-butyl 7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylateHCID 592579207-(4-Methoxycarbonyl-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl esterHCID 68601647HCID 68601647, compound

Product 1

HCID 102491433-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid methyl ester

Procedure

Example 94 (E94) was prepared in an analogous manner to Example 88 (E88) from 7-hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester (WO 02/40471) and 3-bromomethyl-benzoic acid methyl ester using the methods highlighted in Description 3 (D3), Description 4 (D4) and Example 88 (E88); MS (ES+), m/e 380 [M+H]+.

Sources & evidence

ORD record
ord-2412e46fcff44a97a8b20b9b9df1de11
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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