Dihydroisocoumarins—X

Bose, N. K.; Chaudhury, D. N.

doi:10.1016/s0040-4020(01)98395-4

Cited by 9 publications

(1 citation statement)

References 4 publications

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“…3-Isobutylglutaric Anhydride (37). 3-Isobutylglutaric acid (156 g, 829 mmol) and acetyl chloride (130 g, 1.66 mol) were combined and placed under reflux for 16 h. The mixture was placed under atmospheric distillation until a distillate temperature of 135 °C was reached. The mixture was cooled and placed under vacuum distillation to give 37 (129 g, 91.5%): bp 128 °C (1 mmHg); 1 H-NMR (CDCl 3 ) δ 0.91 (d, 6H, J = 6.6 Hz), 1.20−1.24 (m, 2H), 1.52−1.78 (m, 1H), 2.10−2.45 (m, 3H), 2.79−2.91 (m, 2H); 13 C NMR (CDCl 3 , 50 MHz) δ 166.53, 43.99, 36.48, 26.79, 25.08, 22.57; IR (neat) 559.3, 592.0, 609.4, 659.5, 837.0, 954.6, 1033.7, 1070.3, 1184.1, 1241.9, 1288.2, 1369.2, 1388.5, 1411.6, 1425.1, 1469.5, 1760.7, 1810.8, 2873.4, 2958.3, 3552.2 cm -1 .…”

Section: Methodsmentioning

confidence: 99%

Chemical Development of CI-1008, an Enantiomerically Pure Anticonvulsant

Hoekstra¹,

Sobieray²,

Schwindt³

et al. 1997

Org. Process Res. Dev.

174

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Development of a manufacturing process for (S)-3-(aminomethyl)-5-methylhexanoic acid, an anticonvulsant, is described. Initial preparation employed an Evans chiral alkylation on (4R,5S)-4-methyl-3-(1-oxo-4-methylpentyl)-5-phenyl-2-oxazolidinone, using benzyl bromoacetate. Use of tert-butyl bromoacetate proved advantageous for large-scale preparation. Route selection for a low-cost manufacturing process was based on "ideal process" cost projections. Four routes were evaluated in the laboratory. Of the four, two were scaled up in the pilot plant, resulting in selection of a route based on synthesis of racemic 3-(aminomethyl)-5-methylhexanoic acid, followed by resolution with (S)-(+)-mandelic acid.

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Section: Methodsmentioning

confidence: 99%