Triethylamine → HCID 59536935, compound

Temperature

0 °C

Of the compound from Example 159A, 2 g (6.59 mmol) were dissolved under argon in 20 ml of THF. The solution was then cooled to 0° C. and 0.918 ml (6.59 mmol) of triethylamine and 0.94 ml (7.24 mmol) of isobutyl chloroformate were added dropwise. The reaction mixture was subsequently stirred at 0° C. for 1 h. Thereafter the suspension was filtered through a Seitz frit into a cooled flask, with washing with a little THF. A second flask was charged with 747 mg (19.76 mmol) of sodium borohydride in 3 ml of water, with ice cooling. With vigorous stirring, the filtrate was slowly added dropwise. After 1 h, the batch was carefully admixed with saturated aqueous sodium hydrogen carbonate solution. It was then extracted with 30 ml of ethyl acetate. The organic phase was washed again once with saturated aqueous sodium hydrogen carbonate solution and once with saturated aqueous sodium chloride solution. It was then dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. Drying in an HV gave 1.74 g (75% of theory) of the title compound in approximately 83% purity.

1. filtrationThereafter the suspension was filtered through a Seitz frit into a cooled flask
2. washwith washing with a little THF
3. additionWith vigorous stirring, the filtrate was slowly added dropwise
4. waitAfter 1 h
5. extractionIt was then extracted with 30 ml of ethyl acetate
6. washThe organic phase was washed again once with saturated aqueous sodium hydrogen carbonate solution and once with saturated aqueous sodium chloride solution
7. dry with materialIt was then dried over sodium sulphate
8. filtrationfiltered
9. customfreed from the solvent on a rotary evaporator
10. customDrying in an HV

ORD record

ord-53ff4a637bff48c1b21781873d7dd321

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202895B2