1,6-Dioxaspiro[2.5]octane → Benzyl({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)carbamate

HRID 2425744Notes

Reaction equation

HRID 2425744 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 59255048Benzyl({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)carbamateYield 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-ef1b49d49afc4235abbd70cb4a2982c5
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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