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

HRID 1416763Notes

Reaction equation

HRID 1416763 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([CH2:34]O)[CH2:33][CH2:32][CH2:31]1.[K+].[Br-]>>[CH:30]1([CH2:34][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])[CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 78130CyclobutylcarbinolHCID 253877Potassium BromideHCID 42813555-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid

Product 1

HCID 675895895-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid cyclobutylmethyl 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 cyclobutylmethanol according to the procedure of Example 1 as an off-white solid; 1H NMR (DMSO) δ 1.01 (d,3H), 1.75(m,4H), 1.92(m,2H), 2.49 (m, 1H), 2.65 (m,1H), 2.85-3.20 (m,4H), 4.09 (d, 2H), 4.85 (bt, 1H), 6.58 (d, 1H), 6.76 (m,2H), 7.35(m,3H), 7.46(s,1H); IR (KBr): 1652 cm- (C=O), 1761 cm-1 (C=O); MS (CI) m/z 490 (MH+). Anal. Calcd. for C25H28ClNO7 : C, 61.29; H, 5.76; N, 2.86; Cl, 7.24. Found: C, 57.13; H, 5.15; N, 2.43; Cl, 6.83.

Sources & evidence

ORD record
ord-23c32190e281434b80a43b5039956234
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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