Phthalimide → HCID 54369707, compound

HRID 234712Notes

Reaction equation

HRID 234712 reaction equation
O[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:4]1.C1(=O)[NH:23]C(=O)C2=CC=CC=C12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH2:23][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:4]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15237992HCID 15237992, compound

Product 1

HCID 54369707HCID 54369707, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2-hydroxymethyl-l,2,3,4-tetrahydronaphthalen-5-yl)oxyacetate (1.15 g), phthalimide (1.22 g) and triphenylphosphine (2.17 g) in tetrahydrofuran (50 ml) was added diethyl azodicarboxylate (1.6 ml) at -20° C. After stirred for 2 h, the mixture was quenched by addition of water. The mixture was extracted with ether. The extract was washed with a saturated aquous solution of sodium chloride, dried over anhydrous magnesium sulfate and evaporated. To a solution of the obtained residue in ethanol (30 ml) was added hydrazine monohydrate (0.7 ml) at room temperature. The mixture was stirred overnight. The mixture was quenched by addition of water (20 ml) and evaporated. The residue was crystallized from 2N hydrochloric acid (20 ml) to give the title compound (700 mg) having the following physical data.

Workup

  1. customthe mixture was quenched by addition of water
  2. extractionThe mixture was extracted with ether
  3. washThe extract was washed with a saturated aquous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. additionTo a solution of the obtained residue in ethanol (30 ml) was added hydrazine monohydrate (0.7 ml) at room temperature
  7. stirringThe mixture was stirred overnight
  8. customThe mixture was quenched by addition of water (20 ml)
  9. customevaporated
  10. customThe residue was crystallized from 2N hydrochloric acid (20 ml)

Sources & evidence

ORD record
ord-cbaff100a4d04d27ae0f5adff75149ad
Source dataset
uspto-grants-1997_01
Patent number
US05596009

Reaction notes

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