Tetrahydrofuran → HCID 86647915, compound

HRID 574948Notes

Reaction equation

HRID 574948 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.C[Mg]Br.O1CC[CH2:25][CH2:24]1>CCOCC>[CH2:24]([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)[CH3:25]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 50999237Benzyl [(4-oxocyclohexyl)methyl]carbamateHCID 178418573HCID 178418573, compound

Product 1

HCID 86647915HCID 86647915, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

Sources & evidence

ORD record
ord-ed874c4fcaab48a39fce6e3cd74112e6
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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