2,5-Dimethoxytetrahydrofuran → 6-pyrrolidin-1-yl-4H-isoquinoline-1,3-dione

HRID 2236926Notes

Reaction equation

HRID 2236926 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[CH2:5]2.CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1.[BH4-].[Na+]>FC(F)(F)C(O)=O>[N:1]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][C:6](=[O:13])[CH2:5]3)[CH2:16][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 4311764Sodium borohydrideHCID 116224226-Aminoisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 686954026-pyrrolidin-1-yl-4H-isoquinoline-1,3-dioneYield 84.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 6-Amino-4H-isoquinoline-1,3-dione (17.6 mg, 0.1 mmol) in trifluoroacetic acid (250 μL) is added 2,5-dimethoxytetrahydrofuran (15 μL, 0.11 mmol). The reaction mixture is shaken for 5 minutes at ambient temperature, followed by addition of sodium borohydride (9 mg, 0.22 mmol). After shaking at ambient temperature for 15 minutes, gas evolution had ceased and the reaction mixture is quenched with saturated bicarbonate solution. Upon quenching, a precipitate formed. The precipitate is filtered off, rinsed with water, and dried to yield 19.5 mg of 6-Pyrrolidin-1-yl-4H-isoquinoline-1,3-dione.

Workup

  1. stirringAfter shaking at ambient temperature for 15 minutes
  2. customthe reaction mixture is quenched with saturated bicarbonate solution
  3. customUpon quenching
  4. customa precipitate formed
  5. filtrationThe precipitate is filtered off
  6. washrinsed with water
  7. customdried

Sources & evidence

ORD record
ord-48c77a1e46f7483d9215ba1155c2bd2e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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