3,4-dihydro-2H-pyran → 2-Tetrahydropyranyl 4-benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylate

HRID 227931Notes

Reaction equation

HRID 227931 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([O:22][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][O:23]3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 106622014-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 231496802-Tetrahydropyranyl 4-benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (1.00 g) was dissolved in dichloromethane (10 mL). To this solution, 3,4-dihydro-2H-pyran (1.20 mL) and p-toluenesulfonic monohydrate (6.3 mg) were sequentially added and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was sequentially washed with a saturated aqueous solution of sodium bicarbonate and saturated brine. The mixture was then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant:hexane:ethyl acetate=4:1) to give 2-tetrahydropyranyl 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylate (1.18 g).

Workup

  1. washThe reaction mixture was sequentially washed with a saturated aqueous solution of sodium bicarbonate and saturated brine
  2. dry with materialThe mixture was then dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluant:hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9caf53b1ef1a44058c53fc4c9fa6d93c
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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