1-(1-Naphthyl)ethyl isocyanate → HCID 86760701, compound

HRID 1784966Notes

Reaction equation

HRID 1784966 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:8]2[O:12][C:11](=[O:13])[C@@:10]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:9]=2[CH:19]=1)([CH3:4])([CH3:3])[CH3:2].[C:24]1([C@H:34]([N:36]=[C:37]=[O:38])[CH3:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:20]([C:7]1[C:8]([OH:12])=[C:9]([C@@:10]2([C:14]([F:16])([F:15])[F:17])[O:18][C:37](=[O:38])[N:36]([C@@H:34]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)[CH3:35])[C:11]2=[O:13])[CH:19]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)([CH3:21])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 1706331-(1-Naphthyl)ethyl isocyanateHCID 7023847HCID 7023847, compound

Product 1

HCID 86760701HCID 86760701, compoundYield 37.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

(R)-(+)-5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one (100 mg, 0.3 mmol), (R)-(−)-1-(1-naphthyl)ethyl isocyanate (58 uL, 0.33 mmol), and 4-dimethylaminopyridine (3.7 mg, 0.03 mmol) were heated at reflux in toluene (1 mL) for 1 h under nitrogen. The resulting solution was evaporated to dryness and the residue purified by chromatography on silica gel with a gradient of ethyl acetate in heptane from 0% to 100% in 20 min. and then with heptane/DCM 3:1. One obtained 60 mg (37%) of white crystals. Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution in dichloromethane.

Workup

  1. customThe resulting solution was evaporated to dryness
  2. customthe residue purified by chromatography on silica gel with a gradient of ethyl acetate in heptane from 0% to 100% in 20 min.

Sources & evidence

ORD record
ord-95541a6909a948f4a82c9ee7d9271731
Source dataset
uspto-grants-2009_03
Patent number
US07504428B2

Reaction notes

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