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

HRID 13558

반응식

HRID 13558 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-db7dbad0b7b94f2588869652ef25d01f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728129B2

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