Triethylamine → Tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate

HRID 587111노트

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HRID 587111 반응식
[OH:1][CH:2]1[CH2:15][C:4]2([CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]2)[CH2:3]1.CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25].[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:23][S:24]([O:1][CH:2]1[CH2:3][C:4]2([CH2:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:5]2)[CH2:15]1)(=[O:26])=[O:25]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 52987765tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

생성물 1

HCID 86730907Tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate수율 99.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (505 mg, 2.37 mmol) was dissolved in DCM (6.0 mL). The solution was cooled to 0° C. with an external ice-bath. Et3N (330 μL, 2.37 mmol) and DMAP (3.0 mg, 0.0237 mmol) were added. Methanesulfonyl chloride (184 μL, 2.37 mmol) was then added dropwise by syringe. The solution was stirred at 0° C. for 2.0 hrs, was then allowed to warm to room temperature and stirred at room temperature for 18 hrs. A saturated solution of NH4Cl (20 mL) was added and stirred at room temperature for 10 min. The layers were separated. The aqueous phase was extracted with DCM (3×30 mL). The combined organic phase was dried over anhydrous Na2SO4, concentrated by evaporation in vacuo to afford tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate (684 mg, 99%) as a white solid.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 18 hrs
  3. stirringstirred at room temperature for 10 min
  4. customThe layers were separated
  5. extractionThe aqueous phase was extracted with DCM (3×30 mL)
  6. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  7. concentrationconcentrated by evaporation in vacuo

출처 및 근거

ORD 기록
ord-f4d7eef048244bc79c788878e5fb1d8b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226923B2

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