1,6-Dioxaspiro[2.5]octane → HCID 59255048, compound

HRID 502899Notes

Reaction equation

HRID 502899 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:19]1[C:21]2([CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH2:20]1>CO>[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:20][C:21]2([OH:19])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH2:16][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1604391,6-Dioxaspiro[2.5]octaneHCID 14809798Benzyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 59255048HCID 59255048, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzyl(piperidin-4-ylmethyl)carbamate (7.77 g, 31.3 mmol, Bose, D. Subhas et al., Tetrahedron Lett., 1990, 31, 6903) and 1,6-dioxaspiro[2.5]octane (4.29 g, 37.6 mmol, Satyamurthy, Nagichettiar et al., Phosphorus Sulfur, 1984, 19, 113) in methanol (93 mL) was stirred at room temperature for 20 h. Then the mixture was refluxed for 8 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was chromatographed on a column of silica gel eluting with methanol/dichloromethane (1:20) to give 5.60 g (49%) of the title compound as a colorless oil.

Workup

  1. temperatureThen the mixture was refluxed for 8 h
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed in vacuo
  4. customThe residue was chromatographed on a column of silica gel eluting with methanol/dichloromethane (1:20)

Sources & evidence

ORD record
ord-d4f72b04d6c74d59b3097ea0e8ff5696
Source dataset
uspto-grants-2010_08
Patent number
US07776885B2

Reaction notes

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