HCID 178418573, compound → HCID 178468180, compound

HRID 928104Notes

Reaction equation

HRID 928104 reaction equation
CON(C)[C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7]1)=[O:5].[CH3:24][Mg]Br>C1COCC1>[C:4]([C@H:6]1[CH2:7][CH2:8][C@H:9]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:11]1)(=[O:5])[CH3:24]

Participants

4

Reactant 2

HCID 178418573HCID 178418573, compound2×HCID 178502729HCID 178502729, compound

Product 1

HCID 178468180HCID 178468180, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl {trans-4-[methoxy(methyl)carbamoyl]cyclohexyl}carbamate (3.43 g, 10.71 mmol) in THF (107 mL) at 0° C. was added methylmagnesium bromide (3.0 M in diethyl ether, 5.35 mL, 16.06 mmol) and the reaction was stirred for one hour at 0° C. An additional portion of methylmagnesium bromide (3.0 M in diethyl ether, 5.35 mL, 16.06 mmol) was then added and the reaction was allowed to warm to room temperature and then stirred for one hour. The reaction was slowly quenched with aqueous saturated ammonium chloride. Water and ethyl acetate were added and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated to afford benzyl (trans-4-acetylcyclohexyl)carbamate that was used without further purification.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for one hour
  3. customThe reaction was slowly quenched with aqueous saturated ammonium chloride
  4. additionWater and ethyl acetate were added
  5. customthe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e6cd24a2b35c4a7b9689aeae7d4b3503
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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