Tetrahydrofuran → 5-Amino-2-(tetrahydro-pyran-4-ylmethyl)-2H-isoquinolin-1-one

HRID 1037772Notes

Reaction equation

HRID 1037772 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:9]2=[O:14])([O-])=O.O.O.[Sn](Cl)Cl.O1CCCC1>>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][CH:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)[C:9]2=[O:14]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 61436Stannous chloride dihydrateHCID 595794195-Nitro-2-(tetrahydro-pyran-4-ylmethyl)-2H-isoquinolin-1-one

Product 1

HCID 595796435-Amino-2-(tetrahydro-pyran-4-ylmethyl)-2H-isoquinolin-1-one

Procedure

5-Nitro-2-(tetrahydro-pyran-4-ylmethyl)-2H-isoquinolin-1-one (0.78 g, 0.0027 mol) and tin dichloride dihydrate (2 g, 0.01 mol) were stirred in tetrahydrofuran (10 mL, 0.1 mol) at room temperature for 24 hours. The mixture was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 solution, separated. The aqueous layer was extracted with EtOAc (50 mL×3). The combined organic layers were dried over Na2SO4, and purified via flash chromatography (40 g of silica gel, 0-100% EtOAc/Hexanes) to give a yellow solid. MS m/z (M+H) 259.2.

Workup

  1. customThe mixture was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 solution
  2. customseparated
  3. extractionThe aqueous layer was extracted with EtOAc (50 mL×3)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. custompurified via flash chromatography (40 g of silica gel, 0-100% EtOAc/Hexanes)
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-dd8f7befc2ce4f1e83153cd3b82fb2da
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

Loading…