1,1-Bis(hydroxymethyl)cyclopropane → 3-(4-Chlorophenyl)-3-(1-hydroxymethylcyclopropylmethoxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one

HRID 1916982Notes

Reaction equation

HRID 1916982 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:29]1([CH2:34]O)([CH2:32][OH:33])[CH2:31][CH2:30]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:28][CH2:34][C:29]3([CH2:32][OH:33])[CH2:31][CH2:30]3)[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 41014371,1-Bis(hydroxymethyl)cyclopropaneHCID 513497043-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one

Product 1

HCID 533185203-(4-Chlorophenyl)-3-(1-hydroxymethylcyclopropylmethoxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-oneYield 63.1%

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 cyclopropane dimethanol (516 mg, 5.05 mmol, 5 equiv.) using General Procedure A and obtained as an off-white solid (305 mg, 63%). 1H NMR (300 MHz, CDCl3): 8.01-7.98 (m, 2H, O2N—C—CH), 7.92-7.89 (m, 1H, C(O)═C═CH), 7.55-7.52 (m, 2H, Ar—H), 7.32-7.29 (m, 2H, Ar—H), 7.19-7.12 (m, 5H, Ar—H), 4.49 (s, 2H, N—CH2), 3.51-3.43 (m, 2H, HOCH2), 2.81 (s, 2H, OCH2), 0.43-0.40 (m, 2H, CH2), 0.22-0.12 (m, 2H, CH2). 13C NMR (75 MHz, CDCl3): 168.54, 145.52, 144.95, 137.47, 135.29, 133.45, 131.87, 130.50, 130.21, 128.98, 128.30, 124.16, 123.60, 123.48, 94.96, 67.84, 42.75, 22.68, 8.94, 8.90 Anal.: calc. for C26H23ClN2O5: C, 65.20; H, 4.84; N, 5.85, Found: C, 64.83; H, 4.92; N, 5.63.

Sources & evidence

ORD record
ord-d964c2251f1c4548b22a686bdbc24ce5
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

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