Lithium hydroxide, monohydrate → 1-((Tert-butoxy)carbonyl)-4-(methoxymethyl)piperidine-4-carboxylic acid

HRID 216059Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1([C:17]([O:19]CC)=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.O.[OH-].[Li+].OS([O-])(=O)=O.[Na+]>C(O)C.O>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:4]([CH2:3][O:2][CH3:1])([C:17]([OH:19])=[O:18])[CH2:5][CH2:6]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 1-tert-butyl 4-ethyl 4-(methoxymethyl)piperidine-1,4-dicarboxylate from step A (732 mg, 2.63 mmol) in 1:2 ethanol/water (9 mL) was added lithium hydroxide monohydrate (700 mg). The mixture was heated to 75° C. for 1 hour. The reaction was cooled to room temperature and poured into 50 mL of sat. aq. NaHSO4. The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated under vacuum to give the title compound as a viscous yellow oil, which was carried on to the next step without further purification. MS (ES+) [M+H]+=274.2.

Workup

temperatureThe reaction was cooled to room temperature
extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-428b13f6040b42368e989495de67813b
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193202B2

Reaction notes

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