Sodium Cyanide → tert-butyl ((3S,4S,5R)-1-(3-((tert-butoxycarbonyl)amino)pyridin-4-yl)-4-cyano-5-methylpiperidin-3-yl)carbamate

HRID 705308

Reaction equation

CS(O[C@@H:6]1[C@@H:11]([CH3:12])[CH2:10][N:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])C(OC(C)(C)C)=O)[CH2:8][C@H:7]1[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])(=O)=O.[C-:42]#[N:43].[Na+]>CN(C=O)C>[C:30]([O:29][C:27]([NH:19][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:13]=1[N:9]1[CH2:10][C@H:11]([CH3:12])[C@H:6]([C:42]#[N:43])[C@H:7]([NH:34][C:35](=[O:36])[O:37][C:38]([CH3:39])([CH3:41])[CH3:40])[CH2:8]1)=[O:28])([CH3:31])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (3R,4R,5S)-1-(3-(bis(tert-butoxycarbonyl)amino)pyridin-4-yl)-3-(tert-butoxycarbonylamino)-5-methylpiperidin-4-yl methanesulfonate (1.0 equiv.) in DMF (0.10 M) was added NaCN (5.0 equiv.). The mixture was stirred at 80° C. for 6 hrs and partitioned between EtOAc and H2O. The organic layer was washed NaCl(sat), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography to yield tert-butyl ((3S,4S,5R)-1-(3-((tert-butoxycarbonyl)amino)pyridin-4-yl)-4-cyano-5-methylpiperidin-3-yl)carbamate in 5% yield. LC/MS (m/z)=432.2 (MH+), Rt=0.73 min.

Workup

custompartitioned between EtOAc and H2O
washThe organic layer was washed NaCl(sat)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
custompurified by ISCO SiO2 chromatography

Sources & evidence

ORD record: ord-c91cc71a31f84444b5119abdf58644a2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173883B2

Linked notes

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