(r/s)-3 (Tert-butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine → HCID 67243054, compound

HRID 1436035Notes

Reaction equation

HRID 1436035 reaction equation
[C:1]([O:5][C:6]([NH:8][CH: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][CH: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 67243428(r/s)-3 (Tert-butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine

Product 1

HCID 67243054HCID 67243054, compoundYield 161.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-22032a70912b48e7bbca183482fe9485
Source dataset
uspto-grants-2009_11
Patent number
US07618984B2

Reaction notes

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