Pyrrolidine → HCID 22340335, compound

HRID 585308Notes

Reaction equation

HRID 585308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=O)[CH:7]=[CH:6]2.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[Na]>O1CCCC1.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:13][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:7]=[CH:6]2

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 769916-Methoxy-2-naphthaldehydeHCID 5360545Sodium

Product 1

HCID 22340335HCID 22340335, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-methoxy-2-naphthaldehyde (3.00 g, 16.1 mmol) and pyrrolidine (2.69 ml, 32.2 mmol) in tetrahydrofuran (32 ml) and acetic acid (16 ml) was added sodium triacetoxyhydroborate. (6.83 g, 32.2 mmol) at 0° C., and the mixture was stirred at room temperature for 7 hours. The solvent was distilled off under reduced pressure, 1N hydrochloric acid was added to the resulting oil, and the mixture was washed with diethyl ether. An 8N aqueous sodium hydroxide solution was added to the aqueous layer, followed by extraction with ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to obtain the titled compound (3.89 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure, 1N hydrochloric acid
  2. additionwas added to the resulting oil
  3. washthe mixture was washed with diethyl ether
  4. additionAn 8N aqueous sodium hydroxide solution was added to the aqueous layer
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b9b67dd492b94c06a8ad8022cafe1ea4
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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