Ethanol → HCID 57174481, compound

HRID 975653Notes

Reaction equation

HRID 975653 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[C:21](OC)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][C@@H:11]([O:13][Si:14]([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[CH:21]=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 53662624HCID 53662624, compound

Product 1

HCID 57174481HCID 57174481, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2S,4R)-1-benzyl-4-(t-butyldimethylsilyloxy)-2-methoxycarbonylpyrrolidine (20 g) in toluene (100 ml) was added dropwise diisobutyl aluminum hydride (1.02M solution in toluene) (112 ml) with stirring at a temperature kept below -60° C. and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added dropwise ethanol (20.1 ml) with stirring at a temperature kept below -60° C. After stirring for 30 minutes at the same temperature, 5N aqueous sodium hydroxide solution was carefully added. This solution was stirred without further cooling until the temperature reached 20° C. (ca. 1.5 hours). The reaction mixture was allowed to stand for 10 minutes. The organic layer was separated, washed with water (100 ml), dried over anhydrous magnesium sulfate and evaporated in vacuo to give a solution of (2R,4S)-1-benzyl-2-formyl-4-(t-butyldimethylsilyloxy)pyrrolidine (ca. 40 ml) in toluene.

Workup

  1. customkept below -60° C.
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. stirringwith stirring at a temperature
  4. customkept below -60° C
  5. additionwas carefully added
  6. stirringThis solution was stirred
  7. temperaturewithout further cooling until the temperature
  8. customreached 20° C.
  9. custom(ca. 1.5 hours)
  10. customThe organic layer was separated
  11. washwashed with water (100 ml)
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-06d870f3f08b4323ae1fb062a2623772
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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