Benzoic acid, 3-amino-, methyl ester → 4-[(5-Chloro-2-fluoro-benzyl)-(3-methoxycarbonyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726224Notes

Reaction equation

HRID 1726224 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([F:35])=[C:31]([CH:34]=1)[CH2:32]Br>>[C:15]([O:14][C:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:1]([CH2:32][C:31]2[CH:34]=[C:27]([Cl:26])[CH:28]=[CH:29][C:30]=2[F:35])[C:2]2[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)[CH2:21][CH2:20]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 27736262-(Bromomethyl)-4-chloro-1-fluorobenzene

Product 1

HCID 689717204-[(5-Chloro-2-fluoro-benzyl)-(3-methoxycarbonyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

Procedure

Using general procedure A with methyl 3-aminobenzoate (2.16 g, 14.3 mmol) and 1-Boc-4-piperidone (2.39 g, 12.0 mmol) followed by general procedure H with the resulting amine and 5-chloro-2-fluorobenzyl bromide (65%, 1.04 g, 3.0 mmol) gave 4-[(5-chloro-2-fluoro-benzyl)-(3-methoxycarbonyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a white foam (911 mg, 47% over 2 steps).

Sources & evidence

ORD record
ord-dc9ea1abc54d4352b9a9cc84e47803a4
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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