Lithium Hydroxide → N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamide

HRID 1969656노트

반응식

HRID 1969656 반응식
[N:1]([CH:4]1[CH:8]([CH3:9])[CH2:7][CH:6]([NH:10][S:11]([CH:14]2[CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH2:5]1)=C=O.[Li+].[OH-]>C1COCC1>[NH2:1][CH:4]1[CH:8]([CH3:9])[CH2:7][CH:6]([NH:10][S:11]([CH:14]2[CH2:15][CH2:16]2)(=[O:13])=[O:12])[CH2:5]1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 86660440N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide

생성물 1

HCID 67216953N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamide수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

To a mixture of N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide (1.00 g, 4.09 mmol, Preparation #NNN.1) in THF (2.0 mL) was added aqueous LiOH (4 N, 20.5 mL, 82 mmol). The reaction was heated to about 50° C. for about 16 h, cooled to ambient temperature and partitioned between water (5 mL) and EtOAc (10 mL). The organic portion was separated and the aqueous portion was extracted with DCM (3×20 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give crude N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamide (0.66 g, 74%) as a white solid: LC/MS (Table 1, Method n) Rt=0.020 min; MS m/z: 219 (M+H)+.

후처리

  1. temperaturecooled to ambient temperature
  2. custompartitioned between water (5 mL) and EtOAc (10 mL)
  3. customThe organic portion was separated
  4. extractionthe aqueous portion was extracted with DCM (3×20 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-7b78a8d480674f17b1f50911b96620de
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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