Benzyl Alcohol → HCID 21054729, compound

HRID 970373Notes

Reaction equation

C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][C:28]([C:34]([F:37])([F:36])[F:35])(C(O)=O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CCN(CC)CC.[CH2:45]([OH:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[N-:53]=[C:54]=[O:55]>C1(C)C=CC=CC=1>[CH2:45]([O:52][C:54]([NH:53][C:28]1([C:34]([F:35])([F:36])[F:37])[CH2:27][CH2:26][N:25]([C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])[CH2:30][CH2:29]1)=[O:55])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Diphenylphosphoryl azide (1.1 equiv.) is added to a solution of 1-(tert-butoxycarbonyl)-4-(trifluoromethyl)piperidine-4-carboxylic acid (3c) (1 equiv.) and Et3N (1 equiv.) in dry toluene at room temperature, and the reaction is warmed gradually to 80° C. The reaction is kept at 80° C. until gas evolution stops, then dry benzyl alcohol (2 equiv.) is added. The reaction is stirred at 80° C. until the isocyanate is consumed, then the solvents are removed in vacuo. The residue is taken up in CH2Cl2 and the solution is washed sequentially with dilute HCl, dilute NaOH, and H2O. The solution is dried (MgSO4) and concentrated in vacuo, and the residue is purified by flash chromatography on silica gel to afford the title compound.

Workup

customis kept at 80° C. until gas evolution
customis consumed
customthe solvents are removed in vacuo
washthe solution is washed sequentially with dilute HCl, dilute NaOH, and H2O
dry with materialThe solution is dried (MgSO4)
concentrationconcentrated in vacuo
customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-a4e448ee4cc9426aa230e512d5b0561e
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312212B2

Reaction notes

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