Hexane → HCID 86596336, compound

HRID 2053587Notes

Reaction equation

HRID 2053587 reaction equation
[CH3:1][C:2]1[N:3]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C([Li])CCC.CCCCCC.[F:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=[O:43])=[CH:40][CH:39]=1.[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[F:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]([OH:43])[CH2:1][C:2]2[N:3]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:4]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C@H:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:6]=2)=[CH:40][CH:39]=1

Participants

8

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 680234-FluorobenzaldehydeHCID 865963352-Methyl-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl EsterHCID 178418339Butyllithium

Product 1

HCID 86596336HCID 86596336, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

To a cold (−70° C.) solution of 2-methyl-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid, tert-butyl ester (253) (3.36 g, 10.0 mmol) in THF is added 1.6M n-butyl lithium in hexane (6.9 mL, 11.0 mmol), and the mixture is stirred for 1 h at −70° C. To the reaction mixture is added 4-fluorobenzaldehyde (1.18 mL, 11.0 mmol), and the mixture is stirred for 1 h at −70° C. and 1 h at RT. To the reaction mixture is added ammonium chloride solution, EtOAc, and the organic layer is separated, and washed with brine, dried (MgSO4), and filtered. The filtrate is rotary evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane: EtOAc (9:1) gives 2.11 g of the product 256. 1H NMR (CDCl3) δ 7.60-7.45 (m, 2H), 7.15-6.90 (m, 10H), 6.85-6.60 (m, 2H), 5.70-5.20 (m, 4H), 3.60-3.10 (m, 2H), 1.18 (s, 9H); MS: m/z 461 (M++1).

Workup

  1. stirringthe mixture is stirred for 1 h at −70° C. and 1 h at RT
  2. customthe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe residue purified by chromatography on silica gel
  7. washelution with dichloromethane: EtOAc (9:1)

Sources & evidence

ORD record
ord-83536ffcb98547aa82abfde498e61233
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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