Phthalimide → HCID 17796589, compound

HRID 1061032Notes

Reaction equation

HRID 1061032 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([CH2:17]O)=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(=O)[NH:42]C(=O)C2=CC=CC=C12.N(C(OCC)=O)=NC(OCC)=O.O.NN>O1CCCC1.C(O)C>[NH2:42][CH2:17][C:15]1[S:14][C:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C:10]=2[CH:16]=1

Participants

8

Reactant 5

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 24654Hydrazine hydrate (1:1)HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 118456061,1-Dimethylethyl 6,7-dihydro-2-(hydroxymethyl)thieno[3,2-c]pyridine-5(4H)-carboxylate

Product 1

HCID 17796589HCID 17796589, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (100 ml), 5-tert-butoxycarbonyl-2-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (2.10 g) was dissolved, followed by the addition of triphenylphosphine (2.66 g) and phthalimide (1.15 g). After the dropwise addition of diethyl azodicarboxylate (1.28 ml), the resulting mixture was stirred at room temperature for 5 hours. After concentration under reduced pressure, the residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby a colorless solid was obtained. The resulting solid was dissolved in ethanol (40 ml). To the solution, hydrazine hydrate (0.39 ml) was added, followed by heating under reflux for 5 hours. After the solid so precipitated was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=25:1), whereby the title compound (448 mg, 21%) was obtained.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby a colorless solid
  3. customwas obtained
  4. temperatureby heating
  5. temperatureunder reflux for 5 hours
  6. customAfter the solid so precipitated
  7. filtrationwas filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column (dichloromethane˜dichloromethane:methanol=25:1), whereby the title compound (448 mg, 21%)
  10. customwas obtained

Sources & evidence

ORD record
ord-bf5d7da3b9de4ea980839150eb25e5df
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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