Acetic Acid → (2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

HRID 2371820Notes

Reaction equation

HRID 2371820 reaction equation
[Cl-].[Li+].C[O:4][C:5](=O)[C@@H:6]1[CH2:10][C@@H:9]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:8][N:7]1[C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17].[BH4-].[Na+].C(O)(=O)C>O1CCCC1.C(O)C>[CH2:19]([O:18][C:16]([N:7]1[CH2:8][C@H:9]([O:11][S:12]([CH3:15])(=[O:13])=[O:14])[CH2:10][C@H:6]1[CH2:5][OH:4])=[O:17])[CH:20]=[CH2:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 10733517(2S,4R)-N-allyloxycarbonyl-4-methanesulfonyloxyproline methyl ester

Product 1

HCID 18639172(2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanolYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium chloride (18.55 g, 437 mmol) and (2S,4R)-N-allyloxycarbonyl-4-methanesulfonyloxyproline methyl ester (67.2 g, 219 mmol) in tetrahydrofuran (280 ml) were successively added sodium borohydride (16.55 g, 437 mmol) and ethanol (420 ml) in one portion. The reaction mixture was stirred at room temperature for 5 hours, cooled to 5° C., treated carefully with acetic acid (25 ml, 437 mmol) to quench the reaction. The solvents were evaporated in vacuo, and the residue partitioned between ethyl acetate (300 ml) and water (300 ml). The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and evaporated to afford the title compound (56.26 g, 92% yield) as an oil.

Workup

  1. temperaturecooled to 5° C.
  2. customto quench
  3. customthe reaction
  4. customThe solvents were evaporated in vacuo
  5. customthe residue partitioned between ethyl acetate (300 ml) and water (300 ml)
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-8fadf326fc7e43ec8c61585581584cb2
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

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