Dichloromethane → Ethyl 1-oxa-6-azaspiro[2,5]octane-6-carboxylate

HRID 1870707Notes

Reaction equation

HRID 1870707 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:15]S([O-])(=O)=O.C[S+](C)C.ClCCl>O>[O:3]1[C:4]2([CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8][CH2:9]2)[CH2:15]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 11745097HCID 11745097, compound

Product 1

HCID 13672926Ethyl 1-oxa-6-azaspiro[2,5]octane-6-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 47% sodium hydroxide (15 ml), ethyl 4-oxopiperidine-1-carboxylate (4.53 ml, 30 mmol), trimethylsulphonium methanesulphonate (7.36 g, 39 mmol) (Syn. Comm., 1985, 15, 749) and dichloromethane (30 ml) was heated to 50° C. for 16 h, cooled, diluted with water (30 ml), and extracted with dichloromethane. The combined extracts were dried over sodium sulphate and evaporated. The residue was purified by flash column chromatography on silica, eluting with 2% methanol/dichloromethane to give the product as a mobile yellow oil (4.0 g), MS (+EI)m /z 185; 1H NMR (360 MHz) (CDCl3) 4.15 (2H, q, J7.1 Hz), 3.78 (2H, brs), 3.46 (1H, ddd, J3.7, 9.6, 13.3 Hz), 2.71 (2H, s), 1.87-1.79 (2H, m), 1.49-1.43 (2H, m), 1.28 (3H, t, J7.1 Hz).

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-93db05cb066348a896987a7e86ac38c3
Source dataset
uspto-grants-2000_08
Patent number
US06100246

Reaction notes

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