Ethyl 4-(4-oxopiperidin-1-yl)benzoate → Ethyl 4-(4-(cyclohexylmethyl)-4-hydroxypiperidin-1-yl)benzoate

HRID 2196746Notes

Reaction equation

HRID 2196746 reaction equation
[CH:1]1([CH2:7][Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:10]=[C:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1>C1COCC1>[CH:1]1([CH2:7][C:11]2([OH:10])[CH2:12][CH2:13][N:14]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=3)[CH2:15][CH2:16]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12717442Ethyl 4-(4-oxopiperidin-1-yl)benzoateHCID 178419664HCID 178419664, compound

Product 1

HCID 16109048Ethyl 4-(4-(cyclohexylmethyl)-4-hydroxypiperidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclohexylmethylmagnesium bromide (1.90 mL of a 2M solution in THF) at −78° C. was treated with ethyl 4-(4-oxo-1-piperidinyl)benzoate (prepared according to the procedure described in Synthesis 1981, 606-608, 0.30 g), and was allowed to warm to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography eluting with 20% ethyl acetate to give the product.

Workup

  1. customprepared
  2. customdescribed in Synthesis 1981, 606-608, 0.30 g), and
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel chromatography
  9. washeluting with 20% ethyl acetate
  10. customto give the product

Sources & evidence

ORD record
ord-dc6c9c2aba1b47f9a8cbf634abfbc7ff
Source dataset
uspto-grants-2012_12
Patent number
US08338466B2

Reaction notes

Loading…