2-Amino-3-(benzyloxy)propan-1-ol → 1-(1-(R)-benzyloxymethyl-2-hydroxyethylamino)-4-cyclohexylbutan-2-(S)-ol

HRID 20367Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].[CH:14]1([CH2:20][CH2:21][C@H:22]2[CH2:24][O:23]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(O)C>[CH2:7]([O:6][CH2:5][C@H:2]([NH:1][CH2:24][C@@H:22]([OH:23])[CH2:21][CH2:20][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:3][OH:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve (R)-(+)-2-amino-3-benzyloxy-1-propanol (317 mg, 1.75 mmol) and 2-(S)-(2-cyclohexylethyl)-oxirane (270 mg, 1.75 mmol) in absolute ethanol (8 mL) and heat at 80° C. in a sealed glass pressure vessel overnight. Concentrate and purify (silica gel chromatography, eluting with 8:92 to 10:90 methanol:dichloromethane) to give the desired compound (336 mg, 57%).

Workup

concentrationConcentrate
custompurify
wash(silica gel chromatography, eluting with 8:92 to 10:90 methanol:dichloromethane)

Sources & evidence

ORD record: ord-0dd0f2b0bb82455580b3219019ff4366
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745438B2

Reaction notes

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