Water → Tert-butyl 1-oxa-6-azaspiro[2.6]nonane-6-carboxylate

HRID 2035403Notes

Reaction equation

HRID 2035403 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[O:9]=[C:10]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]1.O>CS(C)=O>[O:9]1[C:10]2([CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]2)[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 1512679N-Boc-hexahydro-1H-azepin-4-one

Product 1

HCID 57366410Tert-butyl 1-oxa-6-azaspiro[2.6]nonane-6-carboxylateYield 240.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

to a stirred solution of trimethylsulfoxonium iodide (56.1 g, 255 mmol) in anhydrous DMSO (150 ml) was added a mixture of NaH (18.5 gram 1.5 equiv., 60% in mineral oil) under a nitrogen atmosphere. The mixture was stirred at 65° C. for 1 hour, whereafter compound 2 (32 g, 150 mmol) was added as a solution in DMSO (10 ml). The mixture was refluxed overnight under a nitrogen atmosphere. The solution was allowed to reach room temperature, water was added and the mixture was extracted with diethyl ether (3×200 ml). The combined organic layer was washed with H2O, with brine and dried over Na2SO4. The Et2O was evaporated to yield 82.1 gram (32 g, 95%) compound 3. 1H-NMR (300 MHz, CDCl3): δ (ppm)=1.45 (s, 9H, BOC); 1.50-2.10 (m, 6H), 2.60-2.70 (m, 2H), 3.5-3.60 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed overnight under a nitrogen atmosphere
  2. customto reach room temperature
  3. extractionthe mixture was extracted with diethyl ether (3×200 ml)
  4. washThe combined organic layer was washed with H2O, with brine
  5. dry with materialdried over Na2SO4
  6. customThe Et2O was evaporated

Sources & evidence

ORD record
ord-8019f0b1de244834855a5055a6c95c5b
Source dataset
uspto-grants-2013_11
Patent number
US08575148B2

Reaction notes

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