HCID 90386048, compound → HCID 131733398, compound

HRID 2274867Notes

Reaction equation

HRID 2274867 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([C:10]([NH:13][C:14](=[O:24])[O:15][CH:16]2[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)([CH3:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3]>[OH-].[Pd+2].[OH-]>[CH3:3][CH:2]([C:4]1[CH:5]=[C:6]([C:10]([NH:13][C:14](=[O:24])[O:15][CH:16]2[CH:21]3[CH2:20][CH2:19][N:18]([CH2:23][CH2:22]3)[CH2:17]2)([CH3:11])[CH3:12])[CH:7]=[CH:8][CH:9]=1)[CH3:1]

Participants

3

Reactant 1

HCID 90386048HCID 90386048, compound

Product 1

HCID 131733398HCID 131733398, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

Using general procedure F, 1-azabicyclo[2.2.2]oct-3-yl {2-[3-(prop-1-en-2-yl)phenyl]propan-2-yl}carbamate (48.8 mg, 0.146 mmol) and palladium hydroxide (30 mg, 20 wt. % on carbon) gave the title compound as an off-white solid (16 mg, 33%). 1H NMR (400 MHz, CDCl3) δ 7.24 (d, J=5.1 Hz, 3H), 7.10 (d, 1H), 5.12 (s, 1H), 4.63 (s, 1H), 3.54-2.96 (m, 1H), 2.89 (s, 1H), 2.68 (s, 5H), 2.17-1.75 (m, 2H), 1.67 (s, 6H), 1.62-1.30 (m, 2H), 1.24 (d, J=6.9 Hz, 6H), 1.15-0.85 (m, 1H) ppm. 13C NMR (100 MHz, CDCl3) δ 149.1, 128.5, 124.9, 123.1, 122.5, 55.8, 55.6, 46.6, 34.5, 25.6, 24.6, 24.3, 19.7 ppm. Purity: 94% UPLCMS (210 nm); retention time 0.89 min; (M+1) 331.1.

Sources & evidence

ORD record
ord-16433c497cf34e5889c41138d10a0922
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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