Triphenylphosphine → [2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl ester

HRID 496412Notes

Reaction equation

HRID 496412 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[CH:11][C:10]=1[OH:20])([CH3:4])([CH3:3])[CH3:2].[N:22]1([CH2:27][C@@H:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)O)[CH:26]=[CH:25][N:24]=[CH:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>CO.C(Cl)Cl.C1COCC1>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[CH:11][C:10]=1[O:20][C@@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:27][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 707108(R)-2-Imidazol-1-yl-1-phenyl-ethanolHCID 5462977Diethyl azodicarboxylateHCID 20828939(2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl)-carbamic acid tert-butyl ester

Product 1

HCID 60029890[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl esterYield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A round bottom flask was charged with (2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl)-carbamic acid tert-butyl ester (700 mg, 2.40 mmol), (R)-2-imidazol-1-yl-1-phenyl-ethanol (544 mg, 2.89 mmol), triphenylphospine (759 mg, 2.89 mmol) and dry THF (14 mL). After approximately 15 nm, diethylazodicarboxylate (0.46 mL, 2.89 mmol) was added slowly. The reaction was stirred overnight and concentrated to give a yellow oil. Purification by chromatography (10-20% acetone/CH2Cl2 then 5% MeOH/CH2Cl2) afforded the title compound as a white foam (0.850 g, 1.84 mmol, 77%). The structure was confirmed by NMR and mass spectrometry. MS m/z 462 (M++H).

Workup

  1. concentrationconcentrated
  2. customto give a yellow oil
  3. customPurification by chromatography (10-20% acetone/CH2Cl2

Sources & evidence

ORD record
ord-8d2587de47044b4fb0169ff59e3e1e00
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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