Lithium Hydroxide → 1-(Tert-butoxycarbonyl)-4-(2-methoxyethoxy)piperidine-4-carboxylic acid

HRID 216064Notes

Reaction equation

HRID 216064 reaction equation
COCCOC[C:7]1([C:20]([O:22]CC)=[O:21])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.[Li+].[OH-:26]>C(O)C.O.ClCCl>[C:16]([O:15][C:13]([N:10]1[CH2:9][CH2:8][C:7]([O:26][CH2:17][CH2:16][O:15][CH3:13])([C:20]([OH:22])=[O:21])[CH2:12][CH2:11]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 670367621-Tert-butyl 4-ethyl 4-((2-methoxyethoxy)methyl)piperidine-1,4-dicarboxylate

Product 1

HCID 670367781-(Tert-butoxycarbonyl)-4-(2-methoxyethoxy)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-tert-Butyl 4-ethyl 4-((2-methoxyethoxy)methyl)piperidine-1,4-dicarboxylate from step A (1.78 g, 5.15 mmol) was treated with LiOH (0.62 g. 26 mmol) in ethanol (12 mL) and water (24 mL) at 80° C. for 18 hours. The mixture was cooled, diluted with dichloromethane, and washed with sat. aq. NaHSO4. The aqueous phase was back extracted with dichloromethane (3×), and the organics were combined, washed with brine, dried over MgSO4, and concentrated to give the title compound in quantitative yield. MS (ES+) [M+H]+=318.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with sat. aq. NaHSO4
  3. extractionThe aqueous phase was back extracted with dichloromethane (3×)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3a0629bc5b04b5eafb4b7ba9126b12d
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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