tert-butyl (3-((3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yl)oxy)cyclobutyl)carbamate → tert-butyl (3-((3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yl)oxy)cyclobutyl)carbamate

HRID 1846767Notes

Reaction equation

[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][CH:14]3[CH2:17][CH:16]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15]3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:8]([O:13][CH:14]3[CH2:15][CH:16]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:17]3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of tert-butyl (3-((3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yl)oxy)cyclobutyl)carbamate (346 mg, 1 mmol) and wet Pd—C (50%, 200 mg) in MeOH (100 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 (3-((3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yl)oxy)cyclobutyl)carbamate (331 mg, 0.95 mmol, yield 95%). ESI-MS (M+1): 349 calc. for C19H28N2O4 348.

Workup

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

Sources & evidence

ORD record: ord-519643181864489aaac7a0f4b8544aba
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952037B2

Reaction notes

Loading…