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

HRID 846690노트

반응식

HRID 846690 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-db32f40e77e948ae88db8b7a9b96af7f
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05137892

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