Cyclohexene → HCID 178451417, compound

HRID 1846815Notes

Reaction equation

HRID 1846815 reaction equation
C([O:8][C@H:9]1[CH2:12][C@H:11]([C:13]2[N:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[N:14]=2)[CH2:10]1)C1C=CC=CC=1.C1CCCCC=1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>C(O)C.[Pd]>[OH:8][C@H:9]1[CH2:10][C@H:11]([C:13]2[N:17]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[N:14]=2)[CH2:12]1

Participants

6

Reactant 3

HCID 8079CyclohexeneHCID 493570RiboflavinHCID 178451419HCID 178451419, compound

Product 1

HCID 178451417HCID 178451417, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of tert-butyl 2-(trans-3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.47 g, 1.23 mmol), cyclohexene (0.080 g, 0.91 mmol), and 20 wt % Pd (dry basis) on carbon, Degussa type E101 NE/W (2.45 g) in ethanol (5 mL) under argon was heated to 65° C. for 6 h, cooled to RT, and filtered through Celite®. The filtrate was concentrated in vacuo and the resulting oil was purified by silica gel chromatography to give tert-butyl 2-(trans-3-hydroxycyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.31 g, 1.09 mmol, 88% yield) as a white solid.

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fdb0372caf724e5db44a46352424edc4
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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