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

HRID 456775Notes

Reaction equation

HRID 456775 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]2[C@@H:11](I)[C@H:7]([C@@H:8]([C:21]([O:23][CH3:24])=[O:22])[N:9]2[C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[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:21]([O:23][CH3:24])=[O:22])[N:9]2[C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86598925Methyl (1S,3S,4S,6R,7S)-6-acetyloxy-7-iodo-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl (1S,3S,4S,6R,7S)-6-acetyloxy-7-iodo-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate obtained in Example 42-3 (1.73 g) in methanol (20 mL) containing 20% Pd(OH)2 (173 mg) and triethylamine (0.6 mL) was stirred at room temperature for 1.5 hrs under 1 atm pressure with hydrogen.

Sources & evidence

ORD record
ord-d2c23c45c8ee442abd990355049f1f76
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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