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

HRID 1969656ノート

反応式

HRID 1969656 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-7b78a8d480674f17b1f50911b96620de
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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