Triphenylphosphine → HCID 11775454, compound

HRID 2299198Notes

Reaction equation

HRID 2299198 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C@@H:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][C:6]=2[CH:22]=1.[N:23]1[C:32]2[NH:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:26]=[CH:25][C:24]=1[CH2:33][CH2:34]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:23]1[C:32]2[NH:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:26]=[CH:25][C:24]=1[CH2:33][CH2:34][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C@@H:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][C:6]=2[CH:22]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11367331HCID 11367331, compoundHCID 11403711HCID 11403711, compound

Product 1

HCID 11775454HCID 11775454, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (S)-10,11 -dihydro-3-hydroxy-5H-dibenzo[a,d]cycloheptene-10-acetate (200 mg, 0.67 mmole), 2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-1 -ethanol (241 mg, 1.35 mmole), and PPh3 (354 mg, 1.35 mmole) in dry THF (5 mL) was added diisopropyl azodicarboxylate (0.27 mL, 1.35 mmole) at 0° C. The mixture was allowed to warm to RT as the bath warmed. After 18 hr, the mixture was concentrated under reduced pressure. The residue was chromatographed on silica gel (1:4.5 hexanes/Et2O) to give the title compound (94 mg, 31%) as a clear oil: MS (ES) m/e 457 (M+H)+.

Workup

  1. temperaturewarmed
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was chromatographed on silica gel (1:4.5 hexanes/Et2O)

Sources & evidence

ORD record
ord-b93b5e2d4cd340af873f6083127cc490
Source dataset
uspto-grants-2002_12
Patent number
US06495560B1

Reaction notes

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