Sodium Hydroxide → tert-Butyl 4-cyclopropylpiperazine-1-carboxylate

HRID 13558

反応式

HRID 13558 の反応式
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(O[C:17]1(O[Si](C)(C)C)[CH2:19][CH2:18]1)C.[BH3-]C#N.[Na+].[OH-].[Na+]>O.C(O)(=O)C.CO.C1COCC1>[CH:17]1([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH2:19][CH2:18]1

参加物

9

反応物 4

HCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 20294524tert-Butyl 4-cyclopropylpiperazine-1-carboxylate

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A mixture of tert-butyl piperazine-1-carboxylate (75.0 g), THF (500 mL), methanol (500 mL), [(1-ethoxycyclopropyl)oxy]trimethylsilane (161 mL), NaBH3CN (38.0 g), and acetic acid (37 mL) was heated at 60° C. for 5 h. The mixture was cooled to room temperature, treated with water (30 mL) and stirred for 5 min. The mixture was then treated with 1 N NaOH (130 mL) and was further stirred for 15 min. The mixture was concentrated, and the remaining aqueous solution was extracted with CH2Cl2 (500 mL). The organic layer was washed with 1 N NaOH (500 mL). The combined aqueous layers were extracted with CH2Cl2 (150 mL). The combined organic layers were washed with brine (400 mL), dried (Na2SO4), and concentrated to yield the title compound as a white solid.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. stirringwas further stirred for 15 min
  3. concentrationThe mixture was concentrated
  4. extractionthe remaining aqueous solution was extracted with CH2Cl2 (500 mL)
  5. washThe organic layer was washed with 1 N NaOH (500 mL)
  6. extractionThe combined aqueous layers were extracted with CH2Cl2 (150 mL)
  7. washThe combined organic layers were washed with brine (400 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-db7dbad0b7b94f2588869652ef25d01f
出典データセット
uspto-grants-2010_06
特許番号
US07728129B2

関連ノート

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