Hexane → tert-butyl N-(5-methylhex-1-en-3-yl)carbamate

Temperature

-78 °C

To a stirred suspension of methyltriphenyl phosphonium bromide (10.97 g, 30.70 mmol) in anhydrous tetrahydrofuran (200 ml) at -78° C. (dry ice/acetone bath) under an argon atmosphere, was added n butyl lithium (19.8 ml of a 1.55M hexane solution) dropwise over the course of 5 minutes. After 10 minutes, the -78° C. bath was replaced with a 0° C. bath for one half hour, at which time the resulting orange solution was cooled again to -78° C. The solution was then added dropwise by cannula to a stirred -78° C. solution of Boc-leucinal (6.00 g, 27.91 mmol) in anhydrous tetrahydrofuran (30 ml) over the course of one-half hour. The mixture was then allowed to warm to room temperature during a 3 hour period after which water (150 ml) was added. Extraction with hexane (4×100 ml) provided a combined organic phase which was washed with brine (100 ml), dried (Na2SO4, and concentrated to give crude 3-t-butyloxycarbonylamino-5-methylhex-1-ene (6.5 g). Chromatography with ether/hexane (1/9) provided pure 3-t-butyloxycarbonyl-amino-5 methylhex-1-ene (3.71 g, 60%). Mass spectrum: EI, M+ -57=156; CI, (M+H)+ =214.

1. customthe -78° C. bath
2. customwas replaced with a 0° C.
3. customfor one half hour
4. additionwas added
5. extractionExtraction with hexane (4×100 ml)
6. customprovided a combined organic phase which
7. washwas washed with brine (100 ml)
8. dry with materialdried (Na2SO4
9. concentrationconcentrated

ORD record

ord-0b697dcc56074d98849c666537abee9a

Source dataset

uspto-grants-1991_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05036051