Acetic Acid → HCID 57054788, compound

HRID 1078719Notes

Reaction equation

HRID 1078719 reaction equation
C[O:2][C:3](=[O:21])[C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][N:5]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[Cl-].[Li+].[BH4-].[Na+].[C:26](O)(=[O:28])C>O1CCCC1CO.O.C(OCC)(=O)C>[C:17]([O:16][C:14]([N:5]1[CH2:6][C@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:8][C@:4]1([CH2:26][OH:28])[C:3]([OH:2])=[O:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 57054788HCID 57054788, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7360Tetrahydrofurfuryl alcoholSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxyproline methyl ester (10.0 g, 30.9 mmol) in tetrahydrofuran--methanol (1:1, 100 ml) were successively added lithium chloride (3.93 g, 92.8 mmol) and sodium borohydride (3.51 g, 92.8 mmol). The reaction solution was stirred at room temperature for 11 h. Acetic acid (2 ml) was added to the reaction solution, and ethyl acetate and water were added thereto. The mixture was concentrated in vacuo. The residue was dissolved in water and ethyl acetate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to obtain a residue of (2S,4R)-N-tert-butoxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxyproline (9.41 g).

Workup

  1. additionwere added
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionethyl acetate and extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9853c9091ad24a42995e6ad36451466c
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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