proline dl-form → HCID 68897457, compound

HRID 1783762Notes

Reaction equation

HRID 1783762 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:13][CH2:14][CH:15]=O)=[CH:7][N+:8]([O-:12])=[CH:9]2)=[CH:4][CH:3]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:27])(=O)=O)=CC=1.N1CCCC1C(O)=O.[CH2:45]([NH2:48])[CH:46]=[CH2:47].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:63][C:64]([O:67][C:68]([O:70]C(OC(C)(C)C)=O)=O)([CH3:66])[CH3:65]>C1COCC1.C(O)(C)C>[CH2:45]([N:48]([CH2:15][CH:14]([F:27])[CH2:13][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:9]=[N+:8]([O-:12])[CH:7]=1)[C:68](=[O:70])[O:67][C:64]([CH3:66])([CH3:65])[CH3:63])[CH:46]=[CH2:47]

Participants

9

Reactant 6

HCID 614proline dl-formHCID 7853AllylamineHCID 90495Di-tert-butyl dicarbonateHCID 588007N-FluorobenzenesulfonimideHCID 5049666Sodium triacetoxyborohydrideHCID 87616391HCID 87616391, compound

Product 1

HCID 68897457HCID 68897457, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(7-chloro-2-oxidoisoquinolin-4-yl)propanal (6-1)(300 mg, 1.27 mmol, 1.0 equiv) and N-fluorobenzenesulfonimide (442 mg, 1.40 mmol, 1.1 equiv) were dissolved in THF (11.6 mL) and isopropyl alcohol (1.16 mL). To this mixture, was added DL-proline (29.3 mg, 0.26 mmol, 0.2 equiv). The reaction mixture was stirred at room temperature overnight. LCMS showed product. To this reaction mixture, were added allylamine (191 μl, 2.55 mmol, 2.0 equiv) and sodium triacetoxyborohydride (1.08 g, 5.09 mmol, 4.0 equiv). The reaction mixture was stirred at room temperature for 3 hours before (Boc)2O (833 mg, 3.82 mmol, 3 equiv) was added. The resulted reaction mixture was stirred at room temperature overnight. The reaction mixture was then quenched with H2O, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude was purified with silica gel chromatography (EtOAc/Hexane=0->100%) to afford the product (6-2). LRMS m/z (M+H) 395.1 found, 395.2 required.

Workup

  1. additionwas added
  2. customThe resulted reaction mixture
  3. stirringwas stirred at room temperature overnight
  4. customThe reaction mixture was then quenched with H2O
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude was purified with silica gel chromatography (EtOAc/Hexane=0->100%)

Sources & evidence

ORD record
ord-a2a95c90ae01410ab1c0282bc10143e6
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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