Triethylamine → 3-(Boc-amino)-1-methanesulfonylpyrrolidine

HRID 2191566노트

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HRID 2191566 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

생성물 1

HCID 587241113-(Boc-amino)-1-methanesulfonylpyrrolidine수율 127%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

In a 15 mL round-bottomed flask, 3-(tert-butoxycarbonylamino)pyrrolidine (0.50 g, 2.68 mmol) was dissolved in CH2Cl2 (5 mL). Triethylamine (0.45 mL, 3.22 mmol) was added and the reaction mixture was cooled to 0° C. Methanesulfonyl chloride (0.25 mL, 3.22 mmol) was added dropwise and the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was diluted with CH2Cl2 (20 mL) and quenched with 1.0 M aqueous HCl (5 mL). The aqueous layer was extracted with CH2Cl2 then the combined organics were dried over Na2SO4, filtered and concentrated to afford 0.90 g of (1-methanesulfonyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester as a light brown solid which was used without further purification.

후처리

  1. temperaturethe reaction mixture was slowly warmed to room temperature
  2. customquenched with 1.0 M aqueous HCl (5 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialthe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7f48281271484fe093e619007acf2f2b
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329699B2

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