Ethyl 2-(5-((tert-butoxycarbonyl)amino)pyridin-2-yl)acetate → Ethyl {cis-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(O)(=O)C.[Pt]=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][NH:13][C@@H:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
The mixture of ethyl {5-[(tert-butoxycarbonyl)amino]pyridin-2-yl}acetate (3.72 g, 15.6 mmol, step 4 of Example 1) and platinum oxide (300 mg) in ethanol (6 mL) and acetic acid (6 mL) was stirred under hydrogen (4 atom) at room temperature for 8 h. The mixture was filtered through a pad of Celite washing with ethanol and the filtrate was concentrated. The resulting residue was diluted with 2N aqueous sodium hydroxide solution (100 mL), and extracted with dichloromethane (100 mL×3). The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (20:1) to give 2.48 g (65%) of the title compound as a colorless oil. (trans isomer 559 mg, 15% yield)
Workup
- filtrationThe mixture was filtered through a pad of Celite
- washwashing with ethanol
- concentrationthe filtrate was concentrated
- additionThe resulting residue was diluted with 2N aqueous sodium hydroxide solution (100 mL)
- extractionextracted with dichloromethane (100 mL×3)
- dry with materialThe combined organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (20:1)
Sources & evidence
- ORD record
- ord-2a30f998b1d34ba495186161ff7fc25b
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906532B2
Reaction notes
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