p-Toluenesulfonic acid → 1,5-Dioxa-8-azaspiro[5.4]decane benzyl carbamate

HRID 846690Notes

Reaction equation

HRID 846690 reaction equation
[CH2:1]([NH:8][C:9](=[O:11])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13]1.[CH2:18](O)[CH2:19][CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][C:9](=[O:10])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]1[C:14]2([CH2:15][CH2:16][NH:12][CH2:13]2)[O:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 516892Sodium BicarbonateHCID 867460623-Pyrrolidinone benzyl carbamate

Product 1

HCID 867460631,5-Dioxa-8-azaspiro[5.4]decane benzyl carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a round bottom flask were placed 2.00 g (9.1 mmol) of 3-pyrrolidinone benzyl carbamate, from Example 1 Step 2, dissolved in 40 mL of toluene, 1.65 mL (22.8 mmol) of 1,3-propanediol and 0.09 g (0.46 mmol) of p-toluenesulfonic acid. The mixture was heated at 110°-125° C. for 48 hours. The solution was poured into 100 mL of 5% sodium bicarbonate solution, and the product was extracted into ethyl acetate, which was then dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the residue distilled in a kugelrohr apparatus (200° C. @ 2.5 Torr) to afford the title compound, MS: M/Z 295 (M+NH4), which was taken directly to the next step.

Workup

  1. customInto a round bottom flask were placed
  2. temperatureThe mixture was heated at 110°-125° C. for 48 hours
  3. extractionthe product was extracted into ethyl acetate, which
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. customThe solvent was removed under vacuum
  6. distillationthe residue distilled in a kugelrohr apparatus (200° C. @ 2.5 Torr)

Sources & evidence

ORD record
ord-db32f40e77e948ae88db8b7a9b96af7f
Source dataset
uspto-grants-1992_08
Patent number
US05137892

Reaction notes

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