Hexane → 2-Benzyl-6-(cis-3isopropyloxy-4-hydroxypyrrolidine1-yl)pyridine

HRID 1359369Notes

Reaction equation

HRID 1359369 reaction equation
CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[CH2:17]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]2[CH2:34][C@H:33]3[O:35][C:36]([CH3:39])([CH3:38])[O:37][C@H:32]3[CH2:31]2)[N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>C(OCC)C>[CH2:17]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]2[CH2:31][C@H:32]([OH:37])[C@H:33]([O:35][CH:36]([CH3:39])[CH3:38])[CH2:34]2)[N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 697599182-Benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine

Product 1

HCID 697587042-Benzyl-6-(cis-3isopropyloxy-4-hydroxypyrrolidine1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A hexane solution containing 1.5 mol of diisobutylaluminum hydride was added little by little to a solution of 5.0 ml of diethyl ether containing 460 mg of 2-benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine at −20° C. After stirring at room temperature overnight, the reaction solution was poured into an aqueous ammonium chloride solution, and the mixture was filtered through Celite and extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed. Then, the residue was subjected to filtration through silica gel and eluted with ethyl acetate, to give 369 mg of the target compound.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. customthe solvent was removed
  5. filtrationThen, the residue was subjected to filtration through silica gel
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-72f1f1c888a54251a8d13f89f3d8960d
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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