Ammonium Chloride → HCID 10589967, compound

HRID 842311Notes

Reaction equation

HRID 842311 reaction equation
[BH4-].[Li+].[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([O:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:12][C@H:11]1[C:20](OC)=[O:21])=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([O:15][S:16]([CH3:19])(=[O:17])=[O:18])[CH2:12][C@H:11]1[CH2:20][OH:21])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 10589967HCID 10589967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (3.6 g, 163.0 mM) was added to a solution of methyl (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate (26.5 g, 81.5 mM) in anhydrous tetrahydrofuran (300 ml) with ice-cooling in a nitrogen gas stream and the mixture was stirred at room temperature for 3 hours. The reaction mixture was ice-cooled again, the reaction was ceased by adding dropwise a saturated aqueous solution of ammonium chloride carefully and the solvent was removed. The residue was poured into water, the insoluble matters were dissolved using 1N hydrochloric acid, the mixture was extracted with ethyl acetate and the organic layer was washed with 1N hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate. The solvent was removed to give the title compound almost quantitatively (24 g).

Workup

  1. temperaturecooling in a nitrogen gas stream
  2. temperaturecooled again
  3. customthe solvent was removed
  4. additionThe residue was poured into water
  5. dissolutionthe insoluble matters were dissolved
  6. extractionthe mixture was extracted with ethyl acetate
  7. washthe organic layer was washed with 1N hydrochloric acid, water
  8. dry with materiala saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate
  9. customThe solvent was removed

Sources & evidence

ORD record
ord-478ccce7d7004b82a690401964688549
Source dataset
uspto-grants-2002_04
Patent number
US06372914B1

Reaction notes

Loading…