Benzylamine → tert-butyl (4S,5R)-2-(benzylamino)-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

HRID 18725Notes

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.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>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:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of intermediate 59 (5.0 g, 0.0136 mol), benzylamine (4.5 mL, 0.0407 mol) and MeOH (1 mL) is heated at 95° C. for 2 days. The reaction mixture is cooled to RT and purified by chromatography on silica gel; gradient elution with heptane:EtOAc (80:20-50:50) gives 2.81 g of the product 77. 1H NMR (CDCl3) δ 7.55-7.25 (m, 6 H), 7.10-6.85 (m, 8 H), 6.85-6.70 (m, 2 H), 5.50-5.30 (m, 2 H), 4.80-4.55 (m, 2 H), 1.14 (s, 9 H)

Workup

temperatureThe reaction mixture is cooled to RT
custompurified by chromatography on silica gel
washgradient elution with heptane:EtOAc (80:20-50:50)

Sources & evidence

ORD record: ord-01dbbfe5b97b451ba52719ed5dad67d6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741493B2

Reaction notes

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