Benzyl [(4-oxocyclohexyl)methyl]carbamate → HCID 86647915, compound

HRID 1036051Notes

Reaction equation

HRID 1036051 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][CH2:3]1.[CH2:20]([Mg]Br)[CH3:21]>O1CCCC1.CCOCC>[CH2:20]([C:2]1([OH:1])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:4][CH2:3]1)[CH3:21]

Participants

5

Reactant 2

HCID 50999237Benzyl [(4-oxocyclohexyl)methyl]carbamateHCID 178418443HCID 178418443, compound

Product 1

HCID 86647915HCID 86647915, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a vigorous stirring solution of benzyl (4-oxocyclohexyl)methylcarbamate (1 g) in tetrahydrofuran (20 mL) at −78° C. was slowly added 1 M ethylmagnesium bromide (11.48 ml, 11.48 mmol) in ether. After completion of the addition, the mixture was stirred at −78° C. for 2 hours and was warmed to 0° C., and stirred in an ice bath for 30 minutes. The reaction was quenched with a cold NH4Cl aqueous solution. The precipitates were filtered off and washed with ethyl acetate. The filtrate was concentrated. The residue was dissolved in dichloromethane and loaded onto Analogix purification system, and was eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound.

Workup

  1. customat −78° C.
  2. additionAfter completion of the addition
  3. temperaturewas warmed to 0° C.
  4. stirringstirred in an ice bath for 30 minutes
  5. customThe reaction was quenched with a cold NH4Cl aqueous solution
  6. filtrationThe precipitates were filtered off
  7. washwashed with ethyl acetate
  8. concentrationThe filtrate was concentrated
  9. dissolutionThe residue was dissolved in dichloromethane
  10. customloaded onto Analogix purification system
  11. washwas eluted with 0-50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-d19c1d74a51a4dc58441f1a05114ffd5
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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