Methyl Isocyanate → HCID 57647098, compound

HRID 1171160Notes

Reaction equation

HRID 1171160 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=2)[CH:12]=[C:13]([Cl:28])[C:14]=1[CH2:15][C@@H:16]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:17]1=[O:27].[CH3:40][N:41]=[C:42]=[O:43]>C(Cl)Cl>[CH3:40][NH:41][C:42]([N:24]1[CH2:23][CH2:22][CH:21]([N:18]2[CH2:19][CH2:20][C@@H:16]([CH2:15][C:14]3[C:13]([Cl:28])=[CH:12][C:11]([C:29]4[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:37])[F:38])=[CH:31][CH:30]=4)=[CH:10][C:9]=3[Cl:8])[C:17]2=[O:27])[CH2:26][CH2:25]1)=[O:43]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 86629123HCID 86629123, compound

Product 1

HCID 57647098HCID 57647098, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (R)-3-(3,5-Dichloro-4′-trifluoromethoxy-biphenyl-4-ylmethyl)-1-piperidin-4-yl-pyrrolidin-2-one trifluoroacetic acid (Preparation 33) (85 mg, 0.17 mmol) in CH2Cl2 (4 mL) with methyl isocyanate (11 mg, 0.19 mmol). Stir the reaction overnight at room temperature. Quench the reaction with 1N HCl and extract with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Purify the crude by silica gel column chromatography using Hexanes:EtOAc to elute pure product. Remove the solvent to afford 0.035 g (37%) of product. MS (m/e): 544 (M+1).

Workup

  1. customthe reaction overnight at room temperature
  2. customQuench
  3. customthe reaction with 1N HCl
  4. extractionextract with Et2O
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customPurify the crude by silica gel column chromatography
  9. washEtOAc to elute pure product
  10. customRemove the solvent

Sources & evidence

ORD record
ord-6567f505028447bdadfae4c34222f28b
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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