Cyclopentanol → HCID 9915764, compound

HRID 1416729Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:29])[CH2:9][NH:10][CH:11]([CH3:28])[CH2:12][C:13]2[CH:27]=[CH:26][C:16]3[O:17][C:18]([C:23]([OH:25])=[O:24])([C:20]([OH:22])=[O:21])[O:19][C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[CH:30]1(O)[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:30]1([O:24][C:23]([C:18]2([C:20]([O:22][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:21])[O:17][C:16]3[CH:26]=[CH:27][C:13]([CH2:12][CH:11]([NH:10][CH2:9][CH:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[OH:29])[CH3:28])=[CH:14][C:15]=3[O:19]2)=[O:25])[CH2:34][CH2:33][CH2:32][CH2:31]1.[O:17]([CH2:18][CH3:20])[CH2:16][CH3:15].[ClH:1]

Participants

Reactant 2

HCID 7298Cyclopentanol

HCID 42813555-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid

Product 2

HCID 9915764HCID 9915764, compound

HCID 10953452Ether hydrochloride

Procedure

The title compound was prepared from 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid and cyclopentanol as a yellow gum according to the procedure of Example 1, leaving out the final HCl(g) /Et2O hydrochloride salt forming step: 1H NMR (300 MHz, CDCl3): δ 1.07 (d, J=6.2 Hz, 3H), 1.50-2.00 (complex m, 16H), 2.52-2.70 (complex m, 3H), 2.85-2.95 (m, 2H), 4.55-4.65 (m, 1H), 5.29-5.38 (m, 2H), 6.65-6.72 (m, 1H), 6.76 (s, 1H), 6.84 (d, J=8.0 Hz, 1H), 7.18-7.30 (m, 3H), 7.37 (s, 1H); MS (ES) m/z (relative intensity): 558 (M+, 100), 518 (10), 490 (20).

Sources & evidence

ORD record: ord-42101fb9eb65437d9221d1c0599795a3
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914339

Reaction notes

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