Sodium borohydride → HCID 12805918, compound

HRID 904065Notes

Reaction equation

HRID 904065 reaction equation
[CH3:1][C:2]1([CH3:22])[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:4][CH:3]1[C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1.[BH4-].[Na+]>C(O)C>[CH3:20][N:19]([CH3:21])[C:16]1[CH:15]=[CH:14][C:13]([C@H:3]2[CH2:4][C@@H:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:6][C:2]2([CH3:1])[CH3:22])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23333477HCID 23333477, compound

Product 1

HCID 12805918HCID 12805918, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

16 G. of 5,5-dimethyl-2-phenyl-4-(p-dimethylaminophenyl)-1-pyrroline are dissolved in 300 ml. of absolute ethanol and treated with 16 g. of sodium borohydride. The solution is stirred under nitrogen at room temperature for 14 hours. It is subsequently evaporated to dryness under reduced pressure and the residue suspended in water by intensive stirring. The non-dissolved constituent is filtered off, dried and recrystallized, first from n-hexane and then from diisopropyl ether. There is obtained cis-3-(p-dimethylaminophenyl)-2,2-dimethyl-5-phenyl-pyrrolidine, having a melting point of 117°-118° C.

Workup

  1. customIt is subsequently evaporated to dryness under reduced pressure
  2. filtrationThe non-dissolved constituent is filtered off
  3. customdried
  4. customrecrystallized, first from n-hexane

Sources & evidence

ORD record
ord-4c666b663aa945cda44ac83998e84ec9
Source dataset
uspto-grants-1980_10
Patent number
US04230623

Reaction notes

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