Cyclopentane-1,3-diol → HCID 11655275, compound

HRID 2381573Notes

Reaction equation

HRID 2381573 reaction equation
Cl[C:2]1([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:27]1([OH:33])[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28]1>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:2]2([O:32][CH:29]3[CH2:30][CH2:31][CH:27]([OH:33])[CH2:28]3)[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[N:3]2[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 100165Cyclopentane-1,3-diolHCID 51349421HCID 51349421, compound

Product 1

HCID 11655275HCID 11655275, compound

Procedure

3-Chloro-3-(4-chlorophenyl)-2-phenethylisoindolin-1-one (256 mg, 0.687 mmol) was reacted with 1,3-cyclopentanediol (0.32 mL, 3.44 mmol.) as for general procedure F and the solvent evaporated under vacuum to leave a clear oil of 3-(4-chlorophenyl)-3-(3-hydroxycyclopentyloxy)-2-phenethylisoindolin-1-one. This was purified by HPLC (76.0 mg, 0.170 mmol., 25%). Rf 0.13 (40:60 EtOAc:petrol). IR: 2359, 1958, 1684, 1601, 1491, 1464 cm−1. 1H NMR (300 Hz, CDCl3); δ 0.95-2.04 (m, 6H, cyclopentanediol C—H), 2.24 (m, 1H, N—CH2—CH2—Ar), 2.81 (m, 1H, N—CH2—CH2—Ar), 3.19 (m, 1H, N—CH2), 3.42 (m, 1H, N—CH2), 3.70-3.83 (m, 1H, HO—C—H), 4.32 (m, 0.5H, C—O—C-h), 4.43 (m, 0.5H, C—O—C—H), 6.95-7.23 (m, 11H, Ar), 7.45 (m, 2H, Ar), 7.81 (m, 1H, Ar). 13C NMR (75 Hz, CDCl3); δ 31.7, 31.9, 32.2, 33.7, 33.9, 34.0, 34.6, 32.7, 35.2 (cyclopentane C), 41.6, 41.7, 41.8, 42.0, 42.1, 43.7, 44.1, 45.7, 50.9 (N—CH2—CH2) 72.3, 72.6, 73.0, 73.2, 73.9, 74.0 (cyclopentane C—O), 94.6, 94.7 (quaternary O—C—N), 123.0, 123.8, 123.9, 124.1, 124.2, 126.8, 128.1, 128.3, 128.4, 128.5, 128.9, 129.0, 129.1, 129.2, 129.2, 130.4, 130.4, 130.4, 132.8, 133.1, 134.9, 137.8, 137.8, 138.3, 139.3, 146.3, 146.3, 149.1 (Ar), 168.4, 168.6, 168.7 (C═O). LC/MS-ES+ m/z 480.2, 478.1, 458.1, 456.1, 293.0. Anal. Calcd. for C28H22ClNO3.0.25H2O: C, 73.04; H, 4.93; N, 3.04%. Found C, 73.24; H, 5.00; N, 3.22%. HRMS (EI) m/z: 455.1288. Found 455.1297.

Workup

  1. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-29ee847e0e334eb1a03ef5d288a59719
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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