Methanol → HCID 13611238, compound

A solution of (S)-2-methoxymethoxybutanedioic acid, bis methoxymethyl ester (10 g, 37.5 mmol) in dry tetrahydrofuran (10 ml) under dry nitrogen was treated with borane dimethylsulphide (8.3 ml, 83 mmol). The solution was heated between 60° C. and 80° C. over a period of 5.5 hours and then cooled in ice and treated dropwise with methanol (50 ml). After effervescence had ceased the solution was stirred at room temperature for 18 hours and the solvent removed under vacuum. The residue was evaporated to dryness with methanol (2×50 ml) and the residue chromatographed on silica, eluting with chloroform-methanol 5:1 to give (S)-1,4-dihydroxy-2-(methoxymethoxy)butane (3.9 g, 69%); IR: υmax (film) 3400, 2940, 2890, 2820, 1470, 1440, 1410, 1380, 1300, 1210, 1150, 1100, 1030, 920 cm-1 ; 1H NMR: δH (CDCl3) 1.78 (2H, m, CH2), 2.96 (2H, s, D2O exchangeable OH's), 3.44 (3H, s, OCH3), 3.5-3.85 (5H, m, CH plus 2×CH2 's), 4.72 (1H, d, J=7 Hz, CH of CH2), 4.77 (1H, d, J=7 Hz, CH of CH2).

1. temperatureThe solution was heated between 60° C. and 80° C. over a period of 5.5 hours
2. temperaturecooled in ice
3. customthe solvent removed under vacuum
4. customThe residue was evaporated to dryness with methanol (2×50 ml)
5. customthe residue chromatographed on silica
6. washeluting with chloroform-methanol 5:1

ORD record

ord-314499f0f5594cf08263ce431c21af40

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04965270