Triphenylphosphine → HCID 15453937, compound

HRID 1870286Notes

Reaction equation

HRID 1870286 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[O:35][N:34]=1.[C:42]([O:46][C:47]([NH:49][CH2:50][CH2:51]O)=[O:48])([CH3:45])([CH3:44])[CH3:43]>O1CCCC1>[C:42]([O:46][C:47]([NH:49][CH2:50][CH2:51][O:32][C:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[O:35][N:34]=1)=[O:48])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178518983HCID 178518983, compound

Product 1

HCID 15453937HCID 15453937, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of triphenylphosphine (0.95 g) in tetrahydrofuran (20 ml) was added diethyl azodicarboxylate (0.63 g) with stirring at 5° C., then stirred at the same temperature for 15 minutes. To a reaction mixture, 3-hydroxy-1,2-benzisoxazole (0.45 g) was added and stirred for 15 minutes, then N-t-butoxycarbonyl ethanolamine (0.53 g) was added and the mixture stirred at room temperature for 24 hour. The solvent was evaporated under reduced pressure and residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent, to give the title compound (0.63 g, 68%).

Workup

  1. stirringstirred at the same temperature for 15 minutes
  2. stirringstirred for 15 minutes
  3. stirringthe mixture stirred at room temperature for 24 hour
  4. customThe solvent was evaporated under reduced pressure and residue
  5. customwas purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent

Sources & evidence

ORD record
ord-53c22f31bb034765bccf25548bcaa88b
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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