Acetic Acid → 1-Acetamido-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

HRID 863521Notes

Reaction equation

HRID 863521 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH2:13][C:12](=O)[CH2:11][CH2:10]2)(=[O:3])[CH3:2].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(O)(=O)C.C([BH3-])#N.[Na+]>C1C=CC=CC=1.CN(C=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 134241118-Acetamido-2-tetralone

Product 1

HCID 196962461-Acetamido-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthaleneYield 69.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 19608675Benzene dimethylformamideSolvent

Procedure

A mixture of 8-acetamido-2-tetralone (0.4 g, 2 mmol), pyrrolidine (0.28 g, 4 mmol) and tosic acid (10 mg) in benzene:DMF (5:1, 12 mL) was heated at reflux with a Dean-Stark trap for 4 h. The solvent was evaporated and the residue dissolved in 1:1 MeOH:THF (10 mL). Acetic acid (1 mL) and sodium cyanoborohydride (0.25 g, 4 mmol) were added, and the reaction stirred for 16 h. The solvent was evaporated and the residue taken up in water:methylene chloride. The aqueous layer was basified with 12.5% NaOH, and back extracted. The combined organic phase was dried over sodium sulfate, filtered and evaporated. The residue solidified upon standing, and was crystallized from tolune:hexane to give the product (0.36 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark trap for 4 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in 1:1 MeOH
  5. customThe solvent was evaporated
  6. extractionback extracted
  7. dry with materialThe combined organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customwas crystallized from tolune

Sources & evidence

ORD record
ord-fa30521bf41b4b8b86dac3d46a1e75a9
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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