Diethyl[[4-[2-[(5-t-butyloxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)carbonyl]aminoethyl]-o-phenylene]dioxy]diacetate → 2-Acetyl-5-t-butoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 1940380Notes

Reaction equation

HRID 1940380 reaction equation
C(C(CC)(OC1C=CC(CCN[C:17]([C:19]2[S:27][C:26]3[CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22][C:21]=3[CH:20]=2)=[O:18])=CC=1OCC([O-])=O)C([O-])=O)C.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=C[CH:48]=1>ClCCl>[C:17]([C:19]1[S:27][C:26]2[CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:22][C:21]=2[CH:20]=1)(=[O:18])[CH3:48]

Participants

4

Reactant 2

HCID 21466095Diethyl[[4-[2-[(5-t-butyloxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)carbonyl]aminoethyl]-o-phenylene]dioxy]diacetateHCID 178418287HCID 178418287, compound

Product 1

HCID 214659752-Acetyl-5-t-butoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of the compound prepared in (a) (847 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-cc8a2d2ef84348d1bc0a2f4254ff330d
Source dataset
uspto-grants-1997_12
Patent number
US05698692

Reaction notes

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