HCID 178418332, compound → HCID 178468163, compound

HRID 2181696Notes

Reaction equation

HRID 2181696 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18](=[O:23])N(OC)C)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][Mg]Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:24])[NH:10][CH2:11][C@H:12]1[CH2:13][CH2:14][C@H:15]([C:18](=[O:23])[CH3:25])[CH2:16][CH2:17]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 178418332HCID 178418332, compoundHCID 178502719HCID 178502719, compound

Product 1

HCID 178468163HCID 178468163, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL flask was charged with 15.2 g (45.4 mmol) trans-[4-(methoxy-methyl-carbamoyl)-cyclohexylmethyl]-carbamic acid benzyl ester and 350 mL anhydrous THF. The soluton was cooled to 0° C. then 33.3 mL (99.9 mmol) 3M CH3MgCl was added dropwise over 10 minutes. The reaction mixture was then stirred for 1 hour at 0° C. then quenched with 20 mL 2N acetic acid and poured into 300 mL water. The aqueous was extracted with ethyl acetate (3×200 mL) and the combined organics were washed with 0.5M HCl (1×100 mL), water (1×100 mL), brine (1×100 mL), dried over Na2SO4 and concentrated to a solid. The solid was recrystalized from IPE and filtered to give 5.5 g of a white solid.

Workup

  1. customthen quenched with 20 mL 2N acetic acid
  2. additionpoured into 300 mL water
  3. extractionThe aqueous was extracted with ethyl acetate (3×200 mL)
  4. washthe combined organics were washed with 0.5M HCl (1×100 mL), water (1×100 mL), brine (1×100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a solid
  7. customThe solid was recrystalized from IPE
  8. filtrationfiltered

Sources & evidence

ORD record
ord-0d0851655e2d482bbdf3c9760b9c5792
Source dataset
uspto-grants-2005_05
Patent number
US06894041B2

Reaction notes

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