Water → HCID 54215364, compound

HRID 618185Notes

Reaction equation

HRID 618185 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:18][C@@H:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:16]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:15]1[C:35](=[O:37])[CH3:36])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]1[CH2:18][C@@H:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:16]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:15]1[CH:35]([OH:37])[CH3:36])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 53899837HCID 53899837, compound

Product 1

HCID 54215364HCID 54215364, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 M lithium aluminiumhydride in tetrahydrofuran (1.5 ml, 1.5 mmol) was added slowly to a solution of (3R,4R)-1-benzyl-3,4-dibenzyloxy-2-acetylpyrrolidine (390 mg, 0.94 mmol) in dry tetrahydrofuran (5 ml) at 0-5° C. Stirring was continued for 11/2 hour at room temperature. Water (1 ml) was slowly added. The mixture was filtered and the filtrate was evaporated to dryness in vacuo to give the title compound as an oil. Purification of the crude product on a silica gel column (Eluent: methylene chloride: ethyl acetate (9:1)) afforded (3R,4R)-1-benzyl-3,4-dibenzyloxy-2-(1-hydroxyethyl)pyrrolidine (90 mg, yield 23%) as an oil.

Workup

  1. custom2 hour
  2. customat room temperature
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2f9b96406bab455fb2b57785553bec1e
Source dataset
uspto-grants-1999_09
Patent number
US05952363

Reaction notes

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