tert-Butyl 4-oxopiperidine-1-carboxylate → 4-(4-Tert-butoxycarbonylmethoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726197Notes

Reaction equation

HRID 1726197 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:17]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>>[C:20]([O:19][C:17]([N:24]1[CH2:29][CH2:28][CH:27]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:16])=[CH:14][CH:13]=2)[CH2:26][CH2:25]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

3

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 22060435Tert-butyl 2-(4-aminophenoxy)acetate

Product 1

HCID 689688324-(4-Tert-butoxycarbonylmethoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl esterYield 95%

Procedure

Using general procedure A, (4-amino-phenoxy)-acetic acid tert-butyl ester (Renodon-Corniere, Axelle; et al., J. Med. Chem., 45, 4, 2002, 944-954) (4.84 g, 21.6 mmol) and 1-Boc-4-piperidone (3.4 g, 17.1 mmol) afforded 4-(4-tert-butoxycarbonylmethoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (6.6 g, 95%).

Sources & evidence

ORD record
ord-55a3b5e3b35847d6814d4e7f2c23aa78
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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