tert-Butyl 4-oxopiperidine-1-carboxylate → 4-[(5-Furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)amino]piperidine-1-carboxylic acid tert-butyl ester

HRID 217192Notes

Reaction equation

HRID 217192 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[C:10]1[O:14][N:13]=[C:12]([CH2:15][NH2:16])[N:11]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([NH:16][CH2:15][C:12]2[N:11]=[C:10]([C:2]3[O:1][C:9]4[CH:8]=[CH:7][N:6]=[CH:5][C:4]=4[CH:3]=3)[O:14][N:13]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 57659462C-(5-furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-yl)methylamine

Product 1

HCID 576595104-[(5-Furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)amino]piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of C-(5-furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-yl)methylamine (Preparation 14, 350 mg, 1.62 mmol) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (322 mg, 1.62 mmol) in anhydrous CH2Cl2 (5 mL) was stirred for 10 min. Na(AcO)3BH (412 mg, 1.94 mmol) was added, then the mixture was stirred for 3 d. Standard aqueous work-up, followed by column chromatography (EtOAc-IH, 1:1) gave the title compound: m/z (ES+)=400.0 [M+H]+.

Sources & evidence

ORD record
ord-986a45128b9144afa2257dab3092ea0b
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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