Triphenylphosphine → HCID 22107118, compound

HRID 1900616Notes

Reaction equation

HRID 1900616 reaction equation
C[C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH:5]([C:12]([OH:14])=O)[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8].[C:19]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:39]1[CH:51]=[CH:50][C:49]2C3C(=CC=CC=3)[CH2:42][C:41]=2[CH:40]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH:15]1[C:16]2[CH2:42][C:41]3[C:40](=[CH:39][CH:51]=[CH:50][CH:49]=3)[C:17]=2[CH:18]=[CH:2][C:3]=1[O:4][CH:5]1[CH2:6][CH:7]([C:9]([O:11][CH3:19])=[O:10])[NH:8][C:12]1=[O:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 755472-HydroxyfluoreneHCID 5462977Diethyl azodicarboxylateHCID 54262066HCID 54262066, compound

Product 1

HCID 22107118HCID 22107118, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of the compound prepared as described in Example 4 (0.462 g), triphenylphosphine (0.864 g), and 2-hydroxyfluorene (0.600 g) in tetrahydrofuran (4.2 ml) was cooled to approximately 1°-2° C., and treated with a solution of diethylazodicarboxylate (0.573 g) in tetrahydrofuran (1.7 ml) over a five minute period. After the addition was complete, the reaction was allowed to warm to room temperature. After about 24 hours, the resulting suspension was filtered, and the insolubles washed with tetrahydrofuran (5 ml) to give 0.526 g of methyl 3-(2-fluorenoxy)-2-pyrrolidone-5-carboxylate. This material was dried in a vacuum oven at 60° C. for approximately 24 hours.

Workup

  1. additionA mixture of the compound
  2. customprepared
  3. temperaturewas cooled to approximately 1°-2° C.
  4. additionAfter the addition
  5. filtrationthe resulting suspension was filtered
  6. washthe insolubles washed with tetrahydrofuran (5 ml)

Sources & evidence

ORD record
ord-33e7027d96084206b735a9fd298dc557
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

Loading…