Methanol → tert-Butyl 4-((2-methoxyphenyl)amino)piperidine-1-carboxylate
Reaction equation
CO[C:3]1C=C[C:6]([NH2:9])=[CH:5][CH:4]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(O[BH-](O[C:34](=[O:36])[CH3:35])OC(=O)C)(=O)C.[Na+].[CH3:38]O>>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([NH:9][C:6]2[CH:5]=[CH:4][CH:3]=[CH:35][C:34]=2[O:36][CH3:38])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]Participants
5
Procedure
To a solution of anisidine (3.1 g, 25.2 mmol) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 25.1 mmol) in methanol (100 mL) was added sodium triacetoxyborohydride (13.4 g, 63.2 mmol) at room temperature. After stirring for 6 h, the resulting suspension was partitioned between ethyl acetate and 1N sodium hydroxide. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 10-20% ethyl acetate in hexane to furnish 4-(2-methoxyphenylamino)-piperidine-1-carboxylic acid tert-butyl ester (2.7 g, 8.8 mmol, 35%) as a pale yellow oil.
Workup
- customthe resulting suspension was partitioned between ethyl acetate and 1N sodium hydroxide
- extractionThe aqueous layer was extracted with ethyl acetate
- washThe combined organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography
- washeluting 10-20% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-6cbdbb9184be4011b7fdd5dca6457d7a
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504411B2
Reaction notes
Loading…