Triphenylphosphine → HCID 18626481, compound

HRID 1859804Notes

Reaction equation

HRID 1859804 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][OH:16])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[C:36](=[O:40])[CH2:35][CH2:34][CH2:33]2.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P(C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)=O>C1COCC1.CCOC(C)=O>[C:7]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O:16][C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[C:36](=[O:40])[CH2:35][CH2:34][CH2:33]3)[N:10]=[CH:9]1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 5462977Diethyl azodicarboxylateHCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Product 1

HCID 18626481HCID 18626481, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to the method of Example 32, Step 1, 3-[1-(triphenylmethyl)-1H-imidazole-4-yl]propanol (see for example, J. Med. Chem., 1996;39: 1220-1226) (2.58 g, 7 mmol) was coupled to 6-hydroxy tetralone (1.30 g, 7 mmol) with diethylazodicarboxylate (1.26 mL, 8 mmol) and triphenylphosphine (2.10 g, 8 mmol) in 10 mL of dry THF to afford, after chromatography (SiO2, 50% EtOAc in hexanes), 2.73 g of a 1:1 mixture of the title compound and Ph3PO as determined by HPLC analysis (C18, 0.1% TFA in H2O:0.1% TFA in AcCN gradient 80:20 to 20:80): title compound, retention time=15.87 minutes (48.2%); Ph3PO, retention time=13.12 minutes (50.1%). CI-MS m/e 279 (Ph3PO), 513 (M++1).

Workup

  1. customto afford

Sources & evidence

ORD record
ord-0a61eddd9a06469490540b01c46010f1
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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