Water → tert-Butyl[(5R,6S,8S)-3-(2-methoxypropan-2-yl)-5-methyl-6-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-yl]carbamate

HRID 340180Notes

Reaction equation

HRID 340180 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[NH:10][C:9]1=[N:21][CH2:22][CH:23](O)[C:24]([O:27][CH3:28])([CH3:26])[CH3:25])([CH3:4])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+].O>C(#N)C>[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[N:10]2[C:23]([C:24]([O:27][CH3:28])([CH3:25])[CH3:26])=[CH:22][N:21]=[C:9]12)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2724130Cornforth reagentHCID 137187577tert-Butyl{(3S,5S,6R)-2-[(2-hydroxy-3-methoxy-3-methylbutyl)imino]-6-methyl-5-phenylpiperidin-3-yl}carbamate

Product 1

HCID 131732081tert-Butyl[(5R,6S,8S)-3-(2-methoxypropan-2-yl)-5-methyl-6-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-yl]carbamateYield 19.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl{(3S,5S,6R)-2-[(2-hydroxy-3-methoxy-3-methylbutyl)imino]-6-methyl-5-phenylpiperidin-3-yl}carbamate (196 mg, 0.47 mmol) in acetonitrile (4.7 mL) was added pyridinium dichromate (880 mg, 2.34 mmol), and the mixture was stirred 1 h at 70° C. The mixture was cooled to ambient temperature and saturated aqueous sodium bicarbonate was added. Water was added, and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 95% water/acetonitrile→15% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (36 mg). MS 400.4 (M+1).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by reverse phase chromatography (C-18, 95% water/acetonitrile→15% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-6cc2bc3becce417b9a221abd6dc6191a
Source dataset
uspto-grants-2014_11
Patent number
US08895572B2

Reaction notes

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