Potassium bisulfate → 2-Carboxy-4-Oxo-5-[2-(N-BOC-4-Piperidinyl)ethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 1741596Notes

Reaction equation

HRID 1741596 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH2:5][CH2:4][N:3]1[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[Li]CCCC.CCOCC.[C:36](=[O:38])=[O:37].OS([O-])(=O)=O.[K+]>C1COCC1.O>[C:36]([C:9]1[S:10][C:6]2[CH2:5][CH2:4][N:3]([CH2:11][CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:2](=[O:1])[C:7]=2[CH:8]=1)([OH:38])=[O:37]

Participants

7

Reactant 4

HCID 516920Potassium bisulfateHCID 105708044-Oxo-5-[2-(N-BOC-4-Piperidinyl)ethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridineHCID 86742199Dry ice diethyl etherHCID 178418339Butyllithium

Product 1

HCID 106928282-Carboxy-4-Oxo-5-[2-(N-BOC-4-Piperidinyl)ethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-4 (3.65 g, 0.01 moles) in THF (100 ml) was treated at -78° with n-BuLi (in hexane) and stirring was continued for 30 minutes. This was then poured into a slurry of Et2O/CO2 and this was stirred for 0.5 hours. A solution of 10% KHSO4 was added, and after stirring for 10 minutes, the reaction mixture was diluted with H2O. The organic phase was separated, washed with H2O, brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with CHCl3 (95)/MeOH(5) to give pure 2-5, Rf 0.5.

Workup

  1. stirringthis was stirred for 0.5 hours
  2. stirringafter stirring for 10 minutes
  3. customThe organic phase was separated
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel eluting with CHCl3 (95)/MeOH(5)
  8. customto give pure 2-5, Rf 0.5

Sources & evidence

ORD record
ord-0bb7c97d41e64446bd5ea38b53de4d47
Source dataset
uspto-grants-1994_08
Patent number
US05334596

Reaction notes

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