1-Phenethylamine, (+)- → (3R,4S,6S)-6-methyl-4-((S)-1-phenylethylamino)tetrahydro-2H-pyran-3-ol

HRID 56445Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (4S)-4-methyl-3,7-dioxabicyclo[4.1.0]heptane (˜3 mL dichloromethane solution, 10 mmol) and (R)-1-phenylethanamine (2.4 g, 20 mmol) in isopropyl alcohol (20 mL) was stirred at 85° C. for 1 week. After that, the solution was cooled to room temperature and purified by prep-HPLC to get the title compound (more polar, 120 mg, 10% for 2 steps) as a yellow solid and a side product (less polar, 400 mg, 32% for 2 steps) as a white solid. MS (ES+) C14H21NO2 requires: 235, found: 236 [M+H]+.

Workup

temperatureAfter that, the solution was cooled to room temperature
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-3c132439f0784d03bbdc268e3b2088f5
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434700B2

Reaction notes

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