cis-1,2-Cyclohexanedimethanol → 3-(4-Chlorophenyl)-3-(2-hydroxymethylcyclohexylmethoxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one

HRID 1916985Notes

Reaction equation

HRID 1916985 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:28])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.[C@@H:29]1([CH2:37]O)[CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]1[CH2:35][OH:36]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:28][CH2:37][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]3[CH2:35][OH:36])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2724019cis-1,2-CyclohexanedimethanolHCID 513497043-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one

Product 1

HCID 671734013-(4-Chlorophenyl)-3-(2-hydroxymethylcyclohexylmethoxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-oneYield 64%

Procedure

The named compound was synthesised from 3-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one (400 mg, 1.01 mmol, 1 equiv.) and cis-1,2-cyclohexane-dimethanol (728 mg, 5.05 mmol, 5 equiv.) using General Procedure A and obtained as a yellow solid (337 mg, 64%). 1H NMR (300 MHz, CDCl3): mixture of diastereoisomers: 8.08-7.93 (m, 3H, O2N—C—CH and C(O)═C═CH), 7.58-7.54 (m, 2H, Ar—H), 7.43-7.36 (m, 2H, Ar—H), 7.23-7.11 (m, 5H, Ar—H), 4.61 and 4.25 (d: AB, J=15.0 Hz, 2H, N—CH2); and 4.59 and 4.36 (d: AB, J=15.0 Hz, 2H, N—CH2), 3.53-3.24 (m, 2H, HO—CH2), 2.87-2.61 (m, 2H, OCH2), 1.87-1.09 (m, 10H, CH). 13C NMR (75 MHz, CDCl3): mixture of diastereoisomers: 168.25, 147.42, 145.37, 145.20, 144.84, 144.76, 137.28, 137.12, 134.97, 134.88, 133.03, 131.55, 131.41, 130.15, 130.10, 129.98, 129.94, 128.81, 128.69, 127.98, 127.92, 123.91, 123.81, 123.33, 123.30, 123.10, 123.06, 95.07, 94.97, 63.91, 63.57, 63.44, 63.31, 42.50, 42.43, 40.77, 39.99, 37.18, 27.40, 27.09, 26.21, 26.16, 23.77, 23.44, 23.29. Anal.: calc. for C29H29ClN2O5+0.3 CH2Cl2+0.1 H2O: C, 64.18; H, 5.49; N, 5.11. Found: C, 64.34; H, 5.49; N, 4.95.

Sources & evidence

ORD record
ord-29f1ed24c95b45bf8024276258c6d7f4
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

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