1-Methyl-1,4-cyclohexadiene → tert-Butyl(phenyl(3-(piperidin-4-ylmethoxy)phenyl)methyl)carbamate

HRID 332713Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:10]1[CH:11]=[C:12]([CH:31]=[CH:32][CH:33]=1)[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18](C(OCC2C=CC=CC=2)=O)[CH2:17][CH2:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1CC=CCC=1>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:10]1[CH:33]=[CH:32][CH:31]=[C:12]([O:13][CH2:14][CH:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of benzyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)-methyl)phenoxy)methyl)piperidine-1-carboxylate (1.12 g, 2.11 mmol) in ethanol (10 mL), was added 10% palladium on charcoal (0.22 g) and 1-methyl1,4-cyclohexadiene (1.18 mL, 10.55 mmol). The reaction mixture was heated to 80° C. for 7 hours. The reaction mixture was filtered through a pad of celite, and the filter-pad washed with further ethanol. The filtrate was evaporated at reduced pressure to afford the title compound (0.716 g, 85%).

Workup

filtrationThe reaction mixture was filtered through a pad of celite
washthe filter-pad washed with further ethanol
customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record: ord-3ebdbf2df76e4aab8b0ea63640e4af0f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877774B2

Reaction notes

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