Methyl (1R,3S,4S,6R)-6-acetyloxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate → Methyl (1R,3S,4S,6R)-6-acetyloxy-2-azabicyclo[2.2.1]heptane-3-carboxylate

HRID 456776Notes

Reaction equation

HRID 456776 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]2[CH2:11][C@H:7]([C@@H:8]([C:20]([O:22][CH3:23])=[O:21])[N:9]2[C@@H](C2C=CC=CC=2)C)[CH2:6]1)(=[O:3])[CH3:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:4][C@H:5]1[C@H:10]2[CH2:11][C@H:7]([C@@H:8]([C:20]([O:22][CH3:23])=[O:21])[NH:9]2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 86598926Methyl (1R,3S,4S,6R)-6-acetyloxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86598927Methyl (1R,3S,4S,6R)-6-acetyloxy-2-azabicyclo[2.2.1]heptane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl (1R,3S,4S,6R)-6-acetyloxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate obtained in Example 42-4 (1.25 g) in methanol (20 mL) containing 20% Pd(OH)2 (250 mg) was stirred at room temperature for 17 hrs under 4 atm pressure with hydrogen.

Sources & evidence

ORD record
ord-661779f284474486a8ad55a2d7616011
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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