4-Amino-1-Boc-piperidine → 4-[4-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 502398Notes

Reaction equation

HRID 502398 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17]([C:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)([CH3:21])[CH3:20])=[O:18].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([C:19]([C:17]([O:16][CH3:15])=[O:18])([CH3:21])[CH3:20])=[CH:30][CH:29]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 12682914-Amino-1-Boc-piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 251112114-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoic acid

Product 1

HCID 684547664-[4-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl esterYield 87.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.780 g (3.78 mMol) of 4-amino-piperidine-carboxylic acid tert-butyl ester was suspended in 10 mL of MeCl2 at rt under argon; then, 0.80 g (3.60 mmol) of 4-(1-methoxycarbonyl-1-methyl-ethyl)-benzoic acid, 0.845 g (1.20 eq.) of N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride and 0.583 g (1.30 eq.) of N,N-dimethyl-4-aminopyridine were added. The reaction mixture became a clear solution after stirring for 1 h at rt. After 5 hours, the solution was evaporated i.V. and the residue was purified by chromatography (silicagel, eluent:MeCl2) to yield 1.28 g of the title compound as colorless foam. MS: 405.3 (MH+).

Workup

  1. waitAfter 5 hours
  2. customthe solution was evaporated i.V
  3. customand the residue was purified by chromatography (silicagel, eluent:MeCl2)

Sources & evidence

ORD record
ord-584451639b8e40d58773cd129e745c34
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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