3-Fluorobenzylamine → tert-butyl (4S,5R)-2-[(3-fluorophenyl)methylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

HRID 2053528Notes

Reaction equation

HRID 2053528 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9](SC)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH2:32]>CO>[C:21]([O:20][C:18]([N:10]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:9]1[NH:32][CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[C:28]([F:27])[CH:29]=1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 86596320cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester

Product 1

HCID 68569694tert-butyl (4S,5R)-2-[(3-fluorophenyl)methylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylateYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of intermediate 59 (2.0 g, 5.42 mmol), 3-fluorobenzylamine (1.86 mL, 16.2 mmol) and MeOH (0.5 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and is purified twice by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 1.5 g of the product 87. 1H NMR (CDCl3) δ 7.50 (s, 1H), 7.40-7.30 (m, 1H), 7.30-7.15 (m, 2H), 7.10-6.90 (m, 9H), 7.85-7.75 (m, 2H), 5.50-5.30 (m, 2H), 4.80-4.55 (m, 2H), 1.15 (s, 9H); MS: m/z 446 (M++1).

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. customis purified twice by chromatography on silica gel
  3. washgradient elution with heptane:EtOAc (70:30-60:40)

Sources & evidence

ORD record
ord-352bc8b5946647b4990ee9a58dab3312
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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