Lithium Hydroxide → HCID 22660137, compound

HRID 393458Notes

Reaction equation

HRID 393458 reaction equation
C[O:2][C:3]([C:5]1([CH2:10][CH2:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:13])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[CH3:19][C:17]([CH3:20])([O:16][C:14]([N:12]([CH3:13])[CH2:11][CH2:10][C:5]1([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:15])[CH3:18]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23384151HCID 23384151, compound

Product 1

HCID 22660137HCID 22660137, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-[2-[[(1,1-dimethylethoxy)carbonyl](methyl)amino]ethyl]cyclopentane carboxylic acid methyl ester (4.00 g, 14.0 mmol) in THF/MeOH (2:1, 24 mL) was added a solution of LiOH (1.50 g, 35.0 mmol) in water (8 mL). The mixture was stirred overnight at 50° C. and then cooled to room temperature. The reaction mixture was poured into a round bottom flask and concentrated in vacuo. The mixture was diluted with H2O (50 mL) and acidified with 1M HCl. The aqueous phase was extracted with ethyl acetate (3×150 mL) and the combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography, using hexane-ethyl acetate (5:1), afforded (3.60 g, 95%) of a white powder. HR MS (C14H25NO4): Calcd mass, 272.1862. Obs mass, 272.1872 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. additionThe reaction mixture was poured into a round bottom flask
  3. concentrationconcentrated in vacuo
  4. additionThe mixture was diluted with H2O (50 mL)
  5. extractionThe aqueous phase was extracted with ethyl acetate (3×150 mL)
  6. dry with materialthe combined organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-82c0bbe43f0a4a4888d80db8355f4efe
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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