Water → (2S,4R)-N-methanesulfonyl-4-hydroxy-2-hydroxymethylpyrrolidine

HRID 1638404Notes

Reaction equation

HRID 1638404 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][N:12]1[S:17]([CH3:20])(=[O:19])=[O:18])C.O>O1CCCC1>[CH3:20][S:17]([N:12]1[CH2:13][C@H:14]([OH:16])[CH2:15][C@H:11]1[CH2:10][OH:9])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 13665129(2S,4R)-N-methanesulfonyl-4-hydroxyproline ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 13665131(2S,4R)-N-methanesulfonyl-4-hydroxy-2-hydroxymethylpyrrolidineYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 360 ml of tetrahydrofuran was added 3.98 g (0.105 mol) of lithium aluminum hydride, and the mixture was stirred. To this mixture was slowly added dropwise a solution of 16.6 g (0.07 mol) of (2S,4R)-N-methanesulfonyl-4-hydroxyproline ethyl ester [III] in 200 ml of tetrahydrofuran under agitation and ice-cooling. After stirring the suspension at 0° C. for 3 hours and then at room temperature for 3 hours, 14 ml of water was added dropwise in small portions to the suspension under ice-cooling, and thereafter the mixture was stirred for 30 minutes. Any insoluble matter was removed by filtration and the filtrate was concentrated until dryness under reduced pressure whereby 11.9 g (yield: 87%) of an oily substance was obtained.

Workup

  1. temperaturecooling
  2. stirringAfter stirring the suspension at 0° C. for 3 hours
  3. temperaturecooling
  4. stirringthe mixture was stirred for 30 minutes
  5. customAny insoluble matter was removed by filtration
  6. concentrationthe filtrate was concentrated until dryness under reduced pressure whereby 11.9 g (yield: 87%) of an oily substance
  7. customwas obtained

Sources & evidence

ORD record
ord-65a39665da7e44d1b0825f935b44ec28
Source dataset
uspto-grants-1989_11
Patent number
US04879389

Reaction notes

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