Indoline → (2S,3S)-3-(2,3-dihydro-1H-indol-1-yl)-3-(3-fluorophenyl)propane-1,2-diol

HRID 2110341Notes

Reaction equation

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

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of indoline (1.42 g, 11.89 mmol) and [(2R,3R)-3-(3-fluorophenyl)oxiran-2-yl]methanol (2.0 g, 11.89 mmol) was heated at 125° C. for 5 hours in a sealed reaction vial. Upon cooling, the crude product was dissolved in ethyl acetate, absorbed on Fluorocil, and purified by Biotage chromatography (FlasH40i, silica, 0-55% EtOAc/hexane) to give 2.55 g (75%) of (2S,3S)-3-(2,3-dihydro-1H-indol-1-yl)-3-(3-fluorophenyl)propane-1,2-diol as a colorless oil. MS (ESI) m/z 288.1 ([M+H]+).

Workup

temperatureUpon cooling
customabsorbed on Fluorocil
custompurified by Biotage chromatography (FlasH40i, silica, 0-55% EtOAc/hexane)

Sources & evidence

ORD record: ord-62965793e2cb490d9c4e91472add05e2
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517899B2

Reaction notes

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