HCID 86752622, compound → HCID 67654565, compound

HRID 1292124Notes

Reaction equation

HRID 1292124 reaction equation
[C:1]([C@@:6]12[N:13]([CH3:14])[C@@H:10]([CH2:11][CH2:12]1)[C@H:9]([N:15]=[N+]=[N-])[CH2:8][CH2:7]2)([O:3][CH2:4][CH3:5])=[O:2].[H][H]>[Pd].C(O)C>[C:1]([C@@:6]12[N:13]([CH3:14])[C@@H:10]([CH2:11][CH2:12]1)[C@H:9]([NH2:15])[CH2:8][CH2:7]2)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 86752622HCID 86752622, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67654565HCID 67654565, compoundYield 112.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.5 g of the 1-carbethoxy-4β-azidotropane, 300 mL of ethanol and 1 g of 10% palladium on carbon was shaken under 1 atm of hydrogen (balloon) for 18 h. The mixture was filtered and concentrated under reduced pressure. Drying under vacuum gave 4.5 g of 1-carbethoxy-4β-aminotropane as a gum: 1H NMR (400 MHz, CDCl3) 4.3 (br m, 2H), 4.18 (q, 2H), 3.15 (m, 1H), 1.95 (m, 2H), 1.82 (m, 2H), 1.7 (m, 2H), 1.4 (m, 2H), 1.30 (t, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customDrying under vacuum

Sources & evidence

ORD record
ord-f784343e022948d3a97ca6321aaa240f
Source dataset
uspto-grants-1998_05
Patent number
US05756508

Reaction notes

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