(S)-3-(tert-Butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine → (S)-3-(tert-Butoxycarbonylamino)-1-(4-ethyl-5-isoquinolinesulfonyl)pyrrolidine

HRID 1962443Notes

Reaction equation

HRID 1962443 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([CH:27]=[CH2:28])=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([CH2:27][CH3:28])=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67244957(S)-3-(tert-Butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine

Product 1

HCID 67243053(S)-3-(tert-Butoxycarbonylamino)-1-(4-ethyl-5-isoquinolinesulfonyl)pyrrolidineYield 161.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of Intermediate 6a (120 mg) obtained in Example 9-1, Step A in ethanol (2 ml) was added with 10% palladium/activated carbon (90 mg, Wako Pure Chemical Industries), and the mixture was stirred at room temperature for 72 hours under a hydrogen gas atmosphere. The atmosphere was replaced with nitrogen gas, and then the insoluble solids were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (195 mg).

Workup

  1. customthe insoluble solids were removed by filtration through Celite
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7149d141082042b9b67f3f0209b3454f
Source dataset
uspto-grants-2013_04
Patent number
US08415372B2

Reaction notes

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