Chlorotriethylsilane → HCID 69587134, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of a mixture of 2-amino-5-hydroxymethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester and 2-amino-7-hydroxymethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (1:4 estimated based on 1H-NMR) (200 mg, 0.70 mmol) and diisopropylethylamine (0.25 ml, 1.4 mmol) in dichloromethane (6.0 ml) cooled to 0° C. under nitrogen was added triethylchlorosilane (0.18 ml, 1.1 mmol). The solution was stirred at 0° C. for 5 min. and then stirred at room temperature for 15 min. The solution was washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a 5% mixture of ethyl acetate/hexane as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 42 mg (16%) of 2-amino-5-triethylsilanyloxymethy-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (1) and 193 mg (69%) of 2-amino-7-triethylsilanyloxy-methyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (2).

Provenance & Evidence