Water → HCID 22104561, compound

HRID 1457314Notes

Reaction equation

HRID 1457314 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][C:11]([CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:12]2)=[CH:7][CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.C1(C)C=CC=CC=1>[OH:2][CH2:3][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][C:11]([CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:12]2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 22104515HCID 22104515, compound

Product 1

HCID 22104561HCID 22104561, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[2-(3,4-Dihydro-7-methoxycarbonyl-2-naphthalenyl)ethyl]pyrrolidine (1.0 g) was dissolved in tetrahydrofuran (20 ml), and thereto was added dropwise a 1.5M solution of diisobutyl aluminum hydride in toluene (7.0 ml) under ice-cooling, and the mixture was stirred for one hour. To the reaction solution was added dropwise water to decompose the excess amount of the reducing agent, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol=30:1), and the fractions containing the desired compound were combined, and concentrated under reduced pressure to give the desired compound (0.8 g) as an oily product.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=30:1)
  7. additionthe fractions containing the desired compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2d0e986fe964e4c8a1bb921662d98b5
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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