Acetic Acid → Phenylmethyl (2S,4R)-2-(hydroxymethyl)-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylate

HRID 620785Notes

Reaction equation

HRID 620785 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[CH2:12]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][C@H:23]1[C:32](O)=[O:33])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C>O1CCCC1>[CH2:12]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][C@H:23]1[CH2:32][OH:33])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 11290841HCID 11290841, compound

Product 1

HCID 15117254Phenylmethyl (2S,4R)-2-(hydroxymethyl)-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylateYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydride (10.7 g) in tetrahydrofuran (600 ml) was added boron trifluoride etherate (43.4 ml) with stirring at 0°-10° C. After stirring for 30 minutes, a solution of (2S,4R)-1-benzyloxycarbonyl-2-carboxy-4-methanesulfonyloxypyrrolidine (66.2 g) in tetrahydrofuran (80 ml) was added to the mixture at 0°-10° C. The mixture was stirred at the same condition for 2 hours. Glacial acetic acid (20 ml) was added to the mixture at 0°-5° C. The reaction mixture was stirred at ambient temperature overnight, poured into ice-water (1 l), extracted with ethyl acetate (400 ml). The organic layer was washed with brine (400 ml), dried over magnesium sulfate and evaporated under reduced pressure to give (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (56.90 g).

Workup

  1. stirringAfter stirring for 30 minutes
  2. stirringThe mixture was stirred at the same condition for 2 hours
  3. stirringThe reaction mixture was stirred at ambient temperature overnight
  4. extractionextracted with ethyl acetate (400 ml)
  5. washThe organic layer was washed with brine (400 ml)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-922673bf51ff4c929d76aebef3d9e20e
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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