HCID 21188415, compound → Methyl 7-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 399089Notes

Reaction equation

HRID 399089 reaction equation
[C:1]([CH:5]1[CH2:10][CH:9]2[N:11](CC3C=C(C)C=C(C)C=3)[CH:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2]>C(O)=O.[Pd]>[C:1]([CH:5]1[CH2:10][CH:9]2[NH:11][CH:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 21188415HCID 21188415, compound

Product 1

HCID 21188453Methyl 7-azabicyclo[2.2.1]heptane-2-carboxylateYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

The product formed in Example 72 was treated with an equal weight of 10% Pd-on-C and refluxed in 96% formic acid for 12 hours. The mixture was filtered, the filtrate was partitioned between 10% aqueous Na2 CO3 and methylene chloride, and the extract dried and evaporated, affording a 48% yield of the title compound. Major (endo) isomer: 1H NMR (CDCl3) δ 4.12 (t, 1H), 3.92 (t, 3H), 3.8 (s, 3H), 3.2 (m, 1H), 2.3 (br s, 1H), 2.2-1.55 (m, 6H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was partitioned between 10% aqueous Na2 CO3 and methylene chloride
  3. customthe extract dried
  4. customevaporated

Sources & evidence

ORD record
ord-9b6c02b3555c47e99fcb09df86aefacb
Source dataset
uspto-grants-1998_10
Patent number
US05817679

Reaction notes

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