Triethylamine → HCID 86652252, compound

A solution of ammonium chloride (154 mg, 2.89 mmol) in water (1.5 mL) then zinc dust (289 mg, 4.44 mmol) were added consecutively to a solution of bromide (92) (prepared as above, assumed to be 2.22 mmol) in tetrahydrofuran (6 mL). The mixture was stirred for 19 hours before filtering the suspension through celite in vacuo. The filter cake was washed with diethyl ether (15 mL). A mixture of brine and 1M hydrochloric acid (1:1, 15 mL) was added to the filtrate then the organic phase separated. The aqueous layer was reextracted with diethyl ether (15 mL) then the combined organic layers were washed with brine (10 mL), then dried (MgSO4), filtered and the majority of solvents removed in vacuo to leave a residue. Dichloromethane (2 mL) was added to the residue followed by triethylamine (0.618 mL, 4.44 mmol) then methanesulfonyl chloride (0.334 mL, 4.44 mmol). The suspension was stirred for 2.25 hours then triethylamine (0.309 mL, 2.22 mmol) and methanesulfonyl chloride (0.172 mL, 2.22 mmol) added. The suspension was stirred for 2.75 hours then triethylamine (0.155 mL, 1.11 mmol) and methanesulfonyl chloride (0.86 mL, 1.11 mmol) added. The suspension was stirred for 50 minutes then diluted with dichloromethane (25 mL), washed with water (10 mL), brine (10 mL), dried (Na2SO4), filtered and reduced in vacuo to leave a pale yellow oil (724 mg). Flash chromatography over silica, eluting with ethyl acetate:heptane mixtures 0:100 to 30:70 gave mesylate (93) as a colourless oil (260 mg, 57%).

1. filtrationbefore filtering the suspension through celite in vacuo
2. washThe filter cake was washed with diethyl ether (15 mL)
3. additionA mixture of brine and 1M hydrochloric acid (1:1, 15 mL)
4. additionwas added to the filtrate
5. customthe organic phase separated
6. washthe combined organic layers were washed with brine (10 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. customthe majority of solvents removed in vacuo
10. customto leave a residue
11. stirringThe suspension was stirred for 2.25 hours
12. stirringThe suspension was stirred for 2.75 hours
13. stirringThe suspension was stirred for 50 minutes
14. washwashed with water (10 mL), brine (10 mL)
15. dry with materialdried (Na2SO4)
16. filtrationfiltered

ORD record

ord-e4ed308bc073418bbbb5842f279e5d24

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501744B2