HCID 68411356, compound → (+/-)-4-(3-Aminopyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyl acetate
Reaction equation
[C:1]([O:4][CH:5]1[CH:10]([CH3:11])[CH2:9][C:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N+:18]([O-])=O)=[CH:7][CH:6]1[NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=[O:3])[CH3:2]>CO.CCOC(C)=O.[Pd]>[C:1]([O:4][CH:5]1[CH:10]([CH3:11])[CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH2:18])[CH2:7][CH:6]1[NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])(=[O:3])[CH3:2]Participants
Procedure
To a degassed solution of (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl acetate (1.0 equiv.) in MeOH and EtOAc (1:1, 0.1M) was added Pd/C (0.1 equiv.) and the reaction was stirred at room temperature under a hydrogen balloon for 3 days. Upon completion, the solution was filtered through a pad of Celite, the pad was washed with ethyl acetate and the filtrate was concentrated. The crude material contained about 10% of the undesired isomer. The crude was dissolved in ethyl acetate (˜20%) and hexanes and heated until all dissolved. The solution was allowed to sit at room temperature for 2 days. The precipitate was then collected to give (+/−)-4-(3-aminopyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyl acetate as the pure product in 59% yield. LC/MS=364.3 (M+H), Rt=0.63 min.
Workup
- filtrationUpon completion, the solution was filtered through a pad of Celite
- washthe pad was washed with ethyl acetate
- concentrationthe filtrate was concentrated
- dissolutionThe crude was dissolved in ethyl acetate (˜20%)
- temperaturehexanes and heated until all dissolved
- waitto sit at room temperature for 2 days
- customThe precipitate was then collected
Sources & evidence
- ORD record
- ord-ee1c89c493354ae894a0e65d9bf8db06
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829193B2
Reaction notes
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