Toluene → tert-Butyl 4-((methylamino)methyl)piperidine-1-carboxylate

Temperature

0 °C

In a 32 mL reaction vial was placed a stir bar and 4-methylcarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (0.97 g) dissolved in 12.8 mL anhydrous THF. The solution was cooled to 0° C. with an ice-bath. A 65% toluene solution of Red-Al (3.66 mL) was added dropwise at 0° C. After the addition was completed, the mixture was stirred under N2 at room temperature until all the starting materials were just consumed. The reaction mixture was worked up with H2O at 0° C., extracted with EtOAc (×3). The EtOAc extract was washed with saturated NaCl solution. After drying over Na2SO4, the organic layer was concentrated to give 550 mg of crude product.

1. customIn a 32 mL reaction
2. additionAfter the addition
3. customwere just consumed
4. customwas worked up with H2O at 0° C.
5. extractionextracted with EtOAc (×3)
6. extractionThe EtOAc extract
7. washwas washed with saturated NaCl solution
8. dry with materialAfter drying over Na2SO4
9. concentrationthe organic layer was concentrated

ORD record

ord-e17b68125d3547aeac8f071b030a1aaa

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410119B2