Cyclopentylmethyl methanesulfonate → HCID 67316416, compound

HRID 74353Notes

Reaction equation

[OH:1][C@@H:2]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=1)[C@H:3]([CH3:16])[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].CS(O[CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)(=O)=O>>[CH:30]1([CH2:29][O:23][C:19]2[CH:18]=[C:17]([C@H:2]([OH:1])[C@H:3]([CH3:16])[CH2:4][N:5]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:6]3=[O:15])[CH:22]=[CH:21][CH:20]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

Reactant 2

HCID 15712513Cyclopentylmethyl methanesulfonate

HCID 58027624HCID 58027624, compound

Product 1

HCID 67316416HCID 67316416, compound

Procedure

2-((2R,3R)-3-Hydroxy-3-(3-hydroxyphenyl)-2-methylpropyl)isoindoline-1,3-dione (82) was reacted with cyclopentylmethyl methanesulfonate following the method described for Example 72 to give 2-((2R,3R)-3-(3-(cyclopentylmethoxy)phenyl)-3-hydroxy-2-methylpropyl)isoindoline-1,3-dione as a colorless oil. Yield (0.295 g, 61%). 1H NMR (400 MHz, DMSO-d6) δ 7.75-7.80 (m, 4H), 7.13 (t, J=7.8 Hz, 1H), 6.83-6.88 (m, 2H), 6.66-6.69 (m, 1H), 5.30 (d, J=4.5 Hz, 1H), 4.38-4.41 (m, 1H), 3.77 (d, J=7.0 Hz, 2H), 3.70 (dd, J=5.5, 13.7 Hz, 1H), 3.40 (dd, J=9.4, 13.7 Hz, 1H), 2.20-2.30 (m, 2H), 1.70-1.78 (m, 2H), 1.46-1.62 (m, 4H), 1.26-1.34 (m, 2H), 0.65 (d, J=6.85 Hz, 3H).

Sources & evidence

ORD record: ord-535c49645bc347e0a35c13eddaa72588
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829244B2

Reaction notes

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