Diisopropylethylamine → 2-(3-Fluoro-5-((4-(5-methylthiophen-2-ylsulfonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)ethanol

A solution of 5-methylthiophene-2-sulfonyl chloride (0.15 g) in DCM (3 mL) was added dropwise to a solution of 2-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-5-fluorophenyl)ethanol (example 55, step c) (0.21 g) and N-ethyl-N-isopropylpropan-2-amine (0.14 mL) in DCM (20 mL). The resulting mixture was stirred for 1 h and the solvent evaporated. The residue was partitioned between ethyl acetate (50 mL) and saturated sodium hydrogen carbonate solution (50 mL). The layers were separated and the aqueous extracted with ethyl acetate (2×50 mL). The combined organics were washed with brine (50 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 47.5:47.5:5 ethyl acetate:isohexane:triethylamine to 95:5 ethyl acetate:triethylamine gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow gum. Yield 0.21 g.

1. customthe solvent evaporated
2. customThe residue was partitioned between ethyl acetate (50 mL) and saturated sodium hydrogen carbonate solution (50 mL)
3. customThe layers were separated
4. extractionthe aqueous extracted with ethyl acetate (2×50 mL)
5. washThe combined organics were washed with brine (50 mL)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by silica gel chromatography
10. washeluting with 47.5:47.5:5 ethyl acetate
11. additionThe fractions containing product
12. customevaporated

ORD record

ord-5340d872206c4d84bbd6ad47fe1d8031

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148373B2