Lithium hydroxide, monohydrate → 73096-18-1

HRID 1927809Notes

Reaction equation

HRID 1927809 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:21])[NH:17][CH:18]([CH3:20])[CH3:19])=[O:10])C1C=CC=CC=1.O.[OH-].[Li+]>C1COCC1.O.C(OCC)(=O)C>[CH:18]([NH:17][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:21])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68707124HCID 68707124, compound

Product 1

HCID 2850978173096-18-1Yield 41%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

(2S)-1-(Isopropylcarbamoyl)pyrrolidine-2-carboxylic acid benzyl ester (528 mg, 1.82 mmol) was dissolved in THF/H2O (9:1, 10 ml). Lithium hydroxide monohydrate (229 mg, 5.46 mmol) was added. After 18 h at room temperature the reaction mixture was diluted with ethyl acetate (50 ml). This solution was washed with 1M KHSO4, water and brine, dried (Na2SO4) and evaporated in vacuo to give a colourless oil identified as the title compound (148 mg, 0.74 mmol, 41%).

Workup

  1. washThis solution was washed with 1M KHSO4, water and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give a colourless oil

Sources & evidence

ORD record
ord-cac58a57979a4c74aa7d9882def4e645
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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