Triethylamine → HCID 131725210, compound

In a glass reaction vessel, 650 milligrams (1.3 mmol) CH3(CH2)10CH2C≡C—C≡C(CH2)11OSi(Me2(CMe3)) was dissolved in 6.5 milliliters THF. To this stirred solution was added 2.0 milliliters TBAF (1 molar solution in THF). After 1 h of stirring, the reaction mixture was filtered and concentrated to 520 milligrams of CH3(CH2)10CH2C≡C—C≡C(CH2)11OH which was used without further purification. In a glass reaction vessel, the CH3(CH2)10CH2C≡C—C≡C(CH2)11OH was dissolved in 6.5 milliliters CH2Cl2 and 150 μL (2.0 mmol) methanesulfonyl chloride and 360 μL (2.6 mmol) triethyl amine were added. The reaction was stirred for 2 h and worked up using CH2Cl2 and brine. The CH2Cl2 layer was dried (MgSO4), filtered, and concentrated to 680 milligrams of CH3(CH2)10CH2C≡C—C≡C(CH2)11OS(O2)CH3 which was used without further purification. In a glass reaction vessel, the CH3(CH2)10CH2C≡C—C≡C(CH2)11OS(O2)CH3 was dissolved in 6.5 milliliters DMF and 570 milligrams (8.8 mmol) sodium azide was added. The reaction was stirred for 20 h and worked up using pentane and brine. The pentane layer was dried (MgSO4), filtered and concentrated. This material was purified using column chromatography eluting with 9% dichloromethane in hexanes to yield 260 milligrams of CH3(CH2)10CH2C≡C—C≡C(CH2)11N3. In a glass reaction vessel, the CH3(CH2)10CH2C≡C—C≡C(CH2)11N3 was dissolved in 10 milliliters THF and 0.5 milliliters water and 330 milligrams (1.3 mmol) triphenyl phosphine was added. After 20 h of stirring, hydrogen chloride gas was bubbled through the mixture for 30 seconds. The resulting solid was filtered and washed with diethyl ether to yield 190 milligrams CH3(CH2)10CH2C≡C—C≡C(CH2)11NH3Cl.

1. filtrationthe reaction mixture was filtered
2. concentrationconcentrated to 520 milligrams of CH3(CH2)10CH2C≡C—C≡C(CH2)11OH which
3. customwas used without further purification
4. customIn a glass reaction vessel
5. stirringThe reaction was stirred for 2 h
6. dry with materialThe CH2Cl2 layer was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated to 680 milligrams of CH3(CH2)10CH2C≡C—C≡C(CH2)11OS(O2)CH3 which
9. customwas used without further purification
10. customIn a glass reaction vessel
11. stirringThe reaction was stirred for 20 h
12. dry with materialThe pentane layer was dried (MgSO4)
13. filtrationfiltered
14. concentrationconcentrated
15. customThis material was purified
16. washeluting with 9% dichloromethane in hexanes

ORD record

ord-130dcd5a7e794cb8a07ad9fba66b8109

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816473B2