1-Phenethylamine, (+)- → HCID 118036275, compound

HRID 56433Notes

Reaction equation

[CH3:1][C:2]1([CH3:9])[CH2:8][CH:7]2[CH:5]([O:6]2)[CH2:4][O:3]1.[C:10]1([C@H:16]([NH2:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(C)C>[CH3:1][C:2]1([CH3:9])[CH2:8][C@@H:7]([OH:6])[C@H:5]([NH:18][C@@H:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:17])[CH2:4][O:3]1.[CH3:1][C:2]1([CH3:9])[CH2:8][C@H:7]([OH:6])[C@@H:5]([NH:18][C@@H:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:17])[CH2:4][O:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4,4-dimethyl-3,7-dioxa-bicyclo[4.1.0]heptane (7.0 g, 54 mmol) and (R)-1-phenylethanamine (9.9 g, 82 mmol) in isopropanol (50 mL) was stirred at 80° C. for 6 days. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elute:petroleum ether:dichloromethane containing 1% ammonia-methanol (7 M), 10:1 to dichloromethane containing 1% ammonia/methanol (7 M) to afford (4R,5R)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-ol (6a) (more polar fraction, 1.5 g) and (4S,5S)-2,2-dimethyl-5-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-4-ol (6b) (less polar fraction, 1.7 g) as a yellow oil. Note: The absolute configuration of the products was assigned randomly. MS (ES+) C15H23NO2 requires: 249, found: 250 [M+H]+. Mobile phase for TLC: ethyl acetate/dichloromethane=2/1.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (
washelute

Sources & evidence

ORD record: ord-5912bb3598984fe99e50495da4685d2d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434700B2

Reaction notes

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