Dimethylformamide → HCID 69462855, compound

HRID 456753Notes

Reaction equation

HRID 456753 reaction equation
[CH2:1]([O:4][C@H:5]1[C@H:10]2[CH2:11][C@H:7]([C@@H:8]([C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[C:26]#[N:27])=[O:20])[N:9]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)[CH:2]=[CH2:3].CN(C)C=[O:31]>O.[Cu]Cl>[C:26]([C@@H:22]1[CH2:23][CH2:24][CH2:25][N:21]1[C:19]([C@@H:8]1[C@H:7]2[CH2:11][C@H:10]([C@H:5]([O:4][CH2:1][C:2](=[O:31])[CH3:3])[CH2:6]2)[N:9]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:20])#[N:27]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86598905tert-Butyl (1R,3S,4S,6R)-6-allyloxy-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 69462855HCID 69462855, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

To a solution of tert-butyl (1R,3S,4S,6R)-6-allyloxy-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 16-1 (277 mg) in dimethylformamide (5.0 mL) and water (0.45 mL), were added palladium(2) chloride (105 mg) and copper(1) chloride (292 mg). The mixture was stirred vigorously in aerobic condition at room temperature for 3 hrs.

Sources & evidence

ORD record
ord-c0e5c198c56e4659844cb5e4fc3716b3
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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