Trimethyl borate → [3-(2-Aminoethyl)phenyl]methanol

Temperature

72.5 °C

To a solution of methyl-3-(cyanomethyl)benzoate (4 grams, 0.023 mol, 1 molequivalent) in 5 ml dry THF, 2M LiBH4 in THF (60 ml, 5 molequivalents) and (MeO)3B (3 ml, 1 molequivalent) were added under nitrogen atmosphere. The reaction mixture was stirred and heated at 70-75° C. for 16-18 hours. After cooling, THF was evaporated, and 2NH2SO4 was added to the residue (to acidify the solution to pH of 1-2). The resulting solution was washed with ether and powdered K2CO3 was added to the aqueous phase until the pH reached 7. NaCl was then added and the solution was extracted with THF. The organic phase was dried over MgSO4 and the solvent was evaporated, to give a 2.3 grams (67%) of a pure product, which was used without purification.

1. temperatureAfter cooling
2. customTHF was evaporated
3. addition2NH2SO4 was added to the residue (
4. washThe resulting solution was washed with ether and powdered K2CO3
5. additionwas added to the aqueous phase until the pH
6. additionNaCl was then added
7. extractionthe solution was extracted with THF
8. dry with materialThe organic phase was dried over MgSO4
9. customthe solvent was evaporated

ORD record

ord-b79dc2eed556461aa335a347ac0aeef2

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088941B2