Methyl iodide → (4-Methyloxan-4-yl)methanamine

A mixture of tetrahydropyran-4-carbonitrile (5.00 g) and THF (50 ml) was admixed at 0° C. with lithium hexamethyldisilazide (1 M, 63 ml) and, after 90 minutes, methyl iodide (4.26 ml) was added dropwise with good cooling. After 12 hours, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was dissolved in THF (200 ml), and lithium aluminum hydride (3.79 g) was added. The mixture was boiled at reflux for 6 hours. Water (3.8 ml) and then sodium hydroxide solution (40%; 3.8 ml) were cautiously added dropwise to the cooled suspension. The precipitate was filtered off and the filtrate was concentrated. This afforded the product with the molecular weight of 129.20 (C7H15NO); MS (ESI): 130 (M+H+).

1. customthe reaction mixture was partitioned between water and ethyl acetate
2. dry with materialThe organic phase was dried over sodium sulfate
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in THF (200 ml)
5. additionlithium aluminum hydride (3.79 g) was added
6. temperatureat reflux for 6 hours
7. additionWater (3.8 ml) and then sodium hydroxide solution (40%; 3.8 ml) were cautiously added dropwise to the cooled suspension
8. filtrationThe precipitate was filtered off
9. concentrationthe filtrate was concentrated
10. customThis afforded the product with the molecular weight of 129.20 (C7H15NO)

ORD record

ord-ed8e2eb06d154167a8247f75120ff5ca

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552199B2