HCID 13645761, compound → HCID 13645762, compound

HRID 1982202Notes

Reaction equation

HRID 1982202 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:18][CH2:19][CH2:20][N:21]=[N+]=[N-])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2]>CCO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:1]([O:3][C:4]([C:6]1([CH2:18][CH2:19][CH2:20][NH2:21])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 13645761HCID 13645761, compound

Product 1

HCID 13645762HCID 13645762, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 3.52 g (10 mmol) of the bromo ester and 1.95 g (30 mmol) NaN3 in 30 ml DMF was stirred overnight at 50°. Upon cooling, the contents were poured into 100 ml H2O and extracted with 2×50 ml Et2O. The organic extracts were washed with brine and dried over MgSO4. Filtration and concentration of the organic material provided 3.09 g crude 1-(3-azidopropyl)-2-phenylcyclohexane carboxylic acid ethyl ester. The crude azide from above (3.09 g) was dissolved in 50 ml EtOH (absolute). Lindlar catalyst (0.5 g) was added and the mixture was subjected to hydrogenation. The solution was filtered through Celite and concentrated in vacuo. The residue was dissolved in Et2O. Dilute hydrochloric acid was added and the organic layer was removed. The aqueous layer was basified and extracted with Et2O (2×50 ml). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford 2.43 g crude material. Distillation (140°-143°/0.3 mm) provides 2.40 g (83%) of 1-(3-aminopropyl)-2-phenylcyclohexanecarboxylic acid ethyl ester as a colorless oil.

Workup

  1. filtrationThe solution was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in Et2O
  4. additionDilute hydrochloric acid was added
  5. customthe organic layer was removed
  6. extractionextracted with Et2O (2×50 ml)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford 2.43 g crude material
  11. distillationDistillation (140°-143°/0.3 mm)

Sources & evidence

ORD record
ord-5e19b72e69124614a2f7c372727dd80d
Source dataset
uspto-grants-1986_06
Patent number
US04595759

Reaction notes

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