Benzyl azide → HCID 57899244, compound

HRID 1802772Notes

Reaction equation

HRID 1802772 reaction equation
[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]#[CH:20])=[CH:8][CH:7]=1.[CH2:22]([N:29]=[N+:30]=[N-:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.C(O)(C)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[N:31]=[N:30][N:29]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 57899230HCID 57899230, compound

Product 1

HCID 57899244HCID 57899244, compoundYield 72.3%

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (E)-3-[4-(1-but-3-ynyl-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester (50 mg, 0.176 mmol) and benzyl azide (23.5 mg, 0.176 mmol) in a mixture of water (0.7 mL) and tert-butanol (0.7 mL) were added a solution of sodium ascorbate (1 M in water, 18 μL) and copper sulfate pentahydrate (4.4 mg). The resulting mixture was stirred vigorously for 16 h, diluted with water, cooled to 0° C., and filtered, and the solid was washed with cold water and dried in vacuo to give (E)-3-(4-{1-[2-(1-benzyl-1H-[1,2,3]triazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (53 mg, 72% yield). LCMS (m/z): 417.2 (M+1).

Workup

  1. filtrationfiltered
  2. washthe solid was washed with cold water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e1097f94d69f41dfa154ccbdede67990
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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