Lithium Hydroxide → 220878-25-1

HRID 393457Notes

Reaction equation

HRID 393457 reaction equation
C[O:2][C:3]([C:5]1([CH2:10][CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[CH3:18][C:16]([CH3:19])([O:15][C:13]([NH:12][CH2:11][CH2:10][C:5]1([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:14])[CH3:17]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23384153HCID 23384153, compound

Product 1

HCID 22660113220878-25-1

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the 1-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]cyclopentane carboxylic acid methyl ester (10.6 g, 39.0 mmol) in THF/MeOH (3:1, 40 mL) was added a solution of LiOH (4.20 g, 98.0 mmol) in water (10 mL). The mixture was stirred for 2.5 h 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 (60 mL) and acidified with 1M HCl. The aqueous phase was extracted with ethyl acetate (3×200 mL) and the combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography, using hexane-ethyl acetate (3:1), afforded 5.80 g (58%) as a white powder. HR MS (C13H23NO4): Calcd mass, 258.1705. Obs mass, 258.1700 [(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 (60 mL)
  5. extractionThe aqueous phase was extracted with ethyl acetate (3×200 mL)
  6. dry with materialthe combined organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography
  10. customafforded 5.80 g (58%) as a white powder

Sources & evidence

ORD record
ord-bf9c91d57fb648fe9e956a7327531f08
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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