HCID 53884272, compound → 2-Acetyl-5-t-butoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 234138Notes

Reaction equation

HRID 234138 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17](NCCC3C=CC(OCC(OCC)=O)=C(OCC(OCC)=O)C=3)=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=C[CH:48]=1>ClCCl>[C:17]([C:15]1[S:14][C:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][C:10]=2[CH:16]=1)(=[O:18])[CH3:48]

Participants

4

Reactant 2

HCID 53884272HCID 53884272, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 214659752-Acetyl-5-t-butoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridineYield 191.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of the compound prepared in (a) (847 mg) in dichloromethane (30 ml) was added Molecular Sieves 4A (3 g), followed by pyridinium chlorochromate (966 mg) under ice-cooling. The mixture was stirred for 40 minutes. After the reaction mixture was filtered through FLORISIL, the filtrate was concentrated to give 772 mg of 2-acetyl-5-t-butoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (yield, 92%).

Workup

  1. temperaturecooling
  2. filtrationAfter the reaction mixture was filtered through FLORISIL
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2ce59e35fdf048fda1e87bc9eb260e69
Source dataset
uspto-grants-1997_01
Patent number
US05594004

Reaction notes

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