Water → HCID 67423460, compound

HRID 880726Notes

Reaction equation

HRID 880726 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([F:23])=[CH:11][C:10]=1[CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:31]([CH3:34])[CH2:32][CH3:33].[OH2:35]>O1CCCC1>[C:32]1([NH:31][C:34]([N:27]2[CH2:26][CH2:25][CH:24]([C:10]3[CH:11]=[C:12]([F:23])[C:13]([O:15][CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:29][CH2:28]2)=[O:35])[CH:4]=[CH:3][CH:2]=[CH:1][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11723DimethylethylamineHCID 67422631HCID 67422631, compound

Product 1

HCID 67423460HCID 67423460, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

65 μl (0.45 mmol, 1.2 eq) of (S)-(−)-phenylethyl isocyanate are added to a solution of 147 mg (0.37 mmol, 1 eq) of 4-(2,4-bis(benzyloxy)-5-fluorophenyl)piperidine in 3 ml of tetrahydrofuran in the presence of 64 μl (0.37 mmol, 1 eq) of dimethylethylamine. The reaction medium is stirred at ambient temperature for 50 minutes. The reaction is stopped by adding 5 ml of water, and then extracted with ethyl acetate. The organic phases are combined and dried over magnesium sulphate. The solvent is evaporated off and the residue is chromatographed on silica gel, elution being carried out with 60/40 heptane/ethyl acetate. 178 mg of 4-(2,4-bis(benzyloxy)-5-fluorophenyl)piperidine-1-carboxylic acid phenylamide are obtained. Yield=89%.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. customThe solvent is evaporated off
  4. customthe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-51ca6f8065c84b1fafd2746169c796a0
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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