Water → 1620401-56-0

Temperature

50 °C

(S)-Methanesulfonic acid 1,5-dimethyl-hex-4-enyl ester (2) (3.21 g, 15.56 mmol) was dissolved in N,N-dimethyl-acetamide (55 mL), 40% methylamine in water (54.9 mL, 622 mmol) was added at RT using a heavy-walled reaction vessel (150 mL) with teflon screw cap. The reaction vessel was sealed, stirred, and heated at 50° C. for 64 h after which the reaction mixture was cooled to 5° C., and the system was opened to monitor the reaction by TLC. The reaction mixture was diluted with Et2O (320 mL), shaken, the organic layer was washed with water (4×100 mL), brine (100 mL), dried with MgSO4, and solvent was concentrated to give the titled compound as an oil (1.974 g, 90%). TLC sample was prepared by taking an aliquot (100 uL) of reaction mixture, diluting with EtOAc (100 uL), washing with brine (500 uL), TLC organic layer. TLC, Hexane-EtOAc, 75:25, product, Rf 0.35. DCM-7 N NH3-MeOH, 90:10, 3 Rf, 0.45 (developed with KMnO4 stain). H1 NMR (CDCl3): • 5.10 (m, 1H), 2.52 (m, 1H), 2.40 (s, 3H), 1.99 (m, 2H), 1.68 (s, 3H), 1.61 (s, 3H), 1.49 (m, 2H), 1.31 (m, 1H), 1.04 (d, 3H, J=6.0 z).

1. customcap
2. customThe reaction vessel was sealed
3. temperaturewas cooled to 5° C.
4. customthe reaction by TLC
5. stirringshaken
6. washthe organic layer was washed with water (4×100 mL), brine (100 mL)
7. dry with materialdried with MgSO4, and solvent
8. concentrationwas concentrated

ORD record

ord-fa3e5cf293084adb85d439f224e48d06

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403755B2