Lithium Hydroxide → HCID 66731651, compound

To a solution of methyl 2-benzylpiperidine-4-carboxylate (7.36 g, 31.55 mmol) and DIPEA (11.02 mL, 63.09 mmol) in DCM (200 mL) was added methyl chloroformate (3.18 mL, 41.01 mmol) in 100 mL DCM over 1 h. The reaction mixture was stirred for 40 min, then washed with satd NaHCO3, dried using a phase separator and evaporated. The residue was dissolved in THF (80 mL) followed by addition of LiOH (1.0 g, 42.0 mmol), MeOH (60 mL) and water (60 mL). The reaction mixture was stirred at room temperature under nitrogen atmosphere for 72 h. After evaporation of solvents, the residue was taken up in water. The pH was adjusted to <2 by addition of HCl (10%). The aqueous phase was then extracted with DCM (×5). The combined organic layers were dried by using a phase separator and evaporated to give 2-benzyl-1-(methoxycarbonyl)piperidine-4-carboxylic acid as an oil. MS m/z 276 (M−H)−.

1. washwashed with satd NaHCO3
2. customdried
3. customevaporated
4. dissolutionThe residue was dissolved in THF (80 mL)
5. stirringThe reaction mixture was stirred at room temperature under nitrogen atmosphere for 72 h
6. customAfter evaporation of solvents
7. additionThe pH was adjusted to <2 by addition of HCl (10%)
8. extractionThe aqueous phase was then extracted with DCM (×5)
9. customThe combined organic layers were dried
10. customevaporated

ORD record

ord-e150b56a574d48cc91bf17c52995ad65

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415378B2