2-Methyl-2-butene → HCID 67297086, compound

HRID 1010623Notes

Reaction equation

HRID 1010623 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:13]2([OH:26])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:4]=1)=[O:2].CC(=CC)C.P([O-])(O)(O)=[O:33].[Na+].Cl([O-])=O.[Na+]>CC(O)(C)C.O>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][C:13]([C:5]2[CH:4]=[C:3]([C:1]([OH:33])=[O:2])[C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)([OH:26])[CH2:14][CH2:15]1)=[O:20])([CH3:23])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86630119HCID 86630119, compound

Product 1

HCID 67297086HCID 67297086, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 1.5 g (4.2 mmol) of tert-butyl 4-(4-formyl-2-naphthyl)-4-hydroxypiperidine-1-carboxylate in 25 mL of 2-methyl-2-propanol was added 2.3 mL (21 mmol) of 2-methyl-2-butene followed by dropwise addition of a solution of 1.00 g (8.45 mmol) of sodium dihydrogen phosphate and 877 mg (59.7 mmol) of sodium chlorite in 15 mL of water. The resulting mixture was stirred at ambient temperature for 2 h then evaporated in vacuo to remove all volatiles. The residue was diluted with water (5 mL) and an aqueous 2 N HCl solution was then added dropwise to the stirred mixture until a pH of 4 was achieved. The aqueous phase was then extracted with ethyl acetate (3×5 mL) and the combined organic layers were washed with brine (25 mL), dried over magnesium sulfate, filtered and evaporated in vacuo to yield the crude title compound as a colorless oil. LC/MS 394.2 (M+23).

Workup

  1. customthen evaporated in vacuo
  2. customto remove all volatiles
  3. additionThe residue was diluted with water (5 mL)
  4. additionan aqueous 2 N HCl solution was then added dropwise to the stirred mixture until a pH of 4
  5. extractionThe aqueous phase was then extracted with ethyl acetate (3×5 mL)
  6. washthe combined organic layers were washed with brine (25 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-90ef5095e5aa4f9b89e4e2d96659df32
Source dataset
uspto-grants-2011_07
Patent number
US07977339B2

Reaction notes

Loading…