tert-butyl 2-(3-(4-methylphenylsulfonamido)cyclobutoxy)-5',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate → Tert-butyl 4-(2-(3-(4-methylphenylsulfonamido)cyclobutoxy)pyridin-3-yl)piperidine-1-carboxylate

HRID 1846822Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:15][CH:14]([O:16][C:17]3[C:22]([C:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:24]=4)=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH:12]2[CH2:15][CH:14]([O:16][C:17]3[C:22]([CH:23]4[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]4)=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of tert-butyl 2-(3-(4-methylphenylsulfonamido)cyclobutoxy)-5′,6′-dihydro-[3,4′-bipyridine]-1′(2′H)-carboxylate (499 mg, 1 mmol) and wet Pd—C (50%, 1.0 g) in MeOH (50 mL) was stirred under H2 (40 psi) at 30° C. overnight then the reaction mixture was filtered through CELITE® and washed with MeOH. The filtrate was concentrated to give tert-butyl 4-(2-(3-(4-methylphenylsulfonamido)cyclobutoxy)pyridin-3-yl)piperidine-1-carboxylate (476 mg, 0.95 mmol, yield 95%). ESI-MS (M+1): 502 calc. for C26H35N3O5S 501.

Workup

filtrationthe reaction mixture was filtered through CELITE®
washwashed with MeOH
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-ed5fd191795f4f57a962d16986c95fd4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952037B2

Reaction notes

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