Cyclopropanemethanol → 5-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid cyclopropylmethyl ester

HRID 1416762Notes

Reaction equation

HRID 1416762 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([CH2:33]O)[CH2:32][CH2:31]1.[K+].[Br-]>>[CH:30]1([CH2:33][O:24][C:23]([C:18]2([C:20]([OH:22])=[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])[CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 75644CyclopropanemethanolHCID 253877Potassium BromideHCID 42813555-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid

Product 1

HCID 676295715-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid cyclopropylmethyl ester

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 cyclopropylmethanol according to the procedure of Example 1 as an off-white solid; 1H NMR (DMSO) δ 0.25 (q,2H), 0.49 (q,2H), 1.01 (d,3H), 1.10 (m,1H), 2.49 (m, 1H), 2.85-3.20 (m,4H), 3.94 (d, 2H) 4.85 (bt, 1H), 6.58 (d, 1H), 6.76 (m,2H), 7.35(m,3H), 7.46(s,1H); IR (KBr): 1653 cm-1 (C=O), 1747 cm-1 (C=O); MS (CI) m/z 476 (MH+). Anal. Calcd. for C24H26ClNO7 : C, 60.57; H, 5.51; N, 2.94; Cl, 7.46. Found: C, 56.38; H, 5.16; N, 2.61; Cl, 7.60.

Sources & evidence

ORD record
ord-0694f2c4a55542e1b193b420e34142ed
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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