ethyl (3R)-piperidine-3-carboxylate → ethyl (3R)-1-{[7-(methoxymethoxy)-2H-chromen-3-yl]methyl}piperidine-3-carboxylate

HRID 217472

Reaction equation

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:15]=O)[CH2:11][O:12]2)=[CH:7][CH:6]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH2:15][N:17]3[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18]3)[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 7-(methoxymethoxy)-2H-chromene-3-carbaldehyde (5.00 g) and ethyl (3R)-piperidine-3-carboxylate (4.20 mL) in dichloroethane (150 mL) was added sodium triacetoxyborohydride (12.0 g), followed by stirring at 80° C. for 4 hours. The reaction liquid was cooled to room temperature and then saturated aqueous NaHCO3 was added thereto, followed by extraction with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the vehicle was evaporated. The residue was purified by silica gel column chromatography (hexane:EtOAc=4:1) to obtain ethyl (3R)-1-{[7-(methoxymethoxy)-2H-chromen-3-yl]methyl}piperidine-3-carboxylate (7.30 g) as a yellow oily substance.

Workup

customThe reaction liquid
temperaturewas cooled to room temperature
extractionfollowed by extraction with chloroform
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customthe vehicle was evaporated
customThe residue was purified by silica gel column chromatography (hexane:EtOAc=4:1)

Sources & evidence

ORD record: ord-5af4ddab628246b4be6b910b01411837
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193378B2

Linked notes

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