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

HRID 1809345Notes

Reaction equation

HRID 1809345 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.[O:19]1[C:21]2([CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH2:20]1>CO>[OH:19][C:21]1([CH2:20][N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:3][CH2:2]2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]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, prepared according to Bose, D. Subhas et al., Tetrahedron Lett., 1990, 31, 6903) and 1,6-dioxaspiro[2.5]octane (4.29 g, 37.6 mmol, prepared according to 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 dichloromethane/methanol (v/v=20/1) to give 5.60 g (49%) of the title compound as 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 dichloromethane/methanol (v/v=20/1)

Sources & evidence

ORD record
ord-b2612b5d28144a91bc773913dc8ae9b8
Source dataset
uspto-grants-2013_01
Patent number
US08362038B2

Reaction notes

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