Tetrahydrofuran → 4-(1,4-Dioxaspiro[4.5]decan-8-yl)-1,3-oxazinan-2-one

HRID 2175511Notes

Reaction equation

HRID 2175511 reaction equation
OCC[CH:4]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])(C)C)[CH:5]1[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1.O1CCCC1.CC(C)([O-])C.[K+]>C(OCC)(=O)C>[O:9]1[C:8]2([CH2:7][CH2:6][CH:5]([CH:4]3[CH2:21][CH2:18][O:17][C:16](=[O:22])[NH:15]3)[CH2:14][CH2:13]2)[O:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 58562554HCID 58562554, compound

Product 1

HCID 585625634-(1,4-Dioxaspiro[4.5]decan-8-yl)-1,3-oxazinan-2-oneYield 86.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 250 mL round bottom flask was charge with tert-butyl (3-hydroxy-1-(1,4-dioxaspiro[4.5]decan-8-yl)propyl)carbamate (2.11 g, 6.69 mmol) and tetrahydrofuran (134 mL). The mixture was cooled to 0° C. and potassium tert-butoxide (900 mg, 8.03 mmol) was added. The mixture was stirred at 0° C. for 2 h. The mixture was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride. Dry organic layer with MgSO4, filter, and concentrate in vacuo to give 4-(1,4-dioxaspiro[4.5]decan-8-yl)-1,3-oxazinan-2-one (1.39 g, 5.76 mmol) as a clear oil.

Workup

  1. washwashed with saturated aqueous ammonium chloride
  2. filtrationDry organic layer with MgSO4, filter
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6c30d93c581a40cba5223639f96d1871
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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