Acetic Acid → HCID 59511942, compound

HRID 1157668Notes

Reaction equation

HRID 1157668 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][N:14]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Na].C(O)(=O)C>C(#N)C.CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][NH:14]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 5360545Sodium2×HCID 59511941HCID 59511941, compound

Product 1

HCID 59511942HCID 59511942, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(1,3-benzodioxol-5-yl)-3,3-dimethyl-3,4-dihydro-2H-pyrrole (363 mg, 1.673 mmol) in acetonitrile (35 mL) add sodium triacetoxyborohydride (390 mg, 1.84 mmol) and stir at room temperature for two days. Then add more sodium triaxetoxyborohydride (390 mg, 1.84 mmol) and acetic acid and stir for 3 h. Add more add sodium triaxetoxyborohydride (390 mg, 1.84 mmol). After 0.5 h dissolve the reaction by adding methanol and load onto an ion-exchange SCX-2 (25 g), wash with methanol and then extract with ammonia in methanol. Concentrate under reduced pressure the basic solution, to afford 289 mg (79%) of the title compound. MS: 220 [M+H]+; 1H NMR (300 MHz, CDCl3): δ 6.90 (s, 1H), 6.72-6.75 (m, 1H), 6.72-6.75 (m, 1H), 5.91 (s, 2H), 4.20-4.25 (m, 1H), 2.68-2.72 (m, 1H), 2.75-2.79 (m, 1H), 1.72-1.98 (m, 2H), 1.45-1.1.53 (m, 1H), 1.10-1.18 (m, 6H).

Workup

  1. stirringstir for 3 h
  2. additionAdd more
  3. dissolutionAfter 0.5 h dissolve
  4. customthe reaction
  5. washwash with methanol
  6. extractionextract with ammonia in methanol
  7. concentrationConcentrate under reduced pressure the basic solution

Sources & evidence

ORD record
ord-2a7fda58382447a393117c11a56de0a1
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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