Acetic Acid → 4-Cyclopropylmorpholine-3-carboxamide

HRID 467840노트

반응식

HRID 467840 반응식
[C:1](O)(=O)[CH3:2].C[SiH](C)C.[C:9]([BH3-])#N.[Na+].Cl.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH:15]1[C:20]([NH2:22])=[O:21]>CO>[CH:2]1([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH:15]2[C:20]([NH2:22])=[O:21])[CH2:1][CH2:9]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 70435TrimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 67166308Morpholine-3-carboxylic acid amide hydrochloride

생성물 1

HCID 671539534-Cyclopropylmorpholine-3-carboxamide수율 47.3%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

2.9 g of molecular sieve 3A, 4.3 g (72 mmol) of acetic acid, 7.6 g (43.2 mmol) of 2(1-ethoxy-cyclopropyl)oxy]trimethylsilane and 4.4 g (31.7 mmol) of sodium cyanoborohydride are added successively to 1.2 g (7.2 mmol) of morpholine-3-carboxylic acid amide hydrochloride (WO2005026156 Hennequin L. F. A. et al.) in solution in methanol (36 ml). The reaction mixture is heated at 70° C. for 3.5 hours, then cooled to room temperature and filtered. The filtrate is concentrated under reduced pressure, then the residue is taken up in dichloromethane (200 ml) and washed 3 times with an aqueous solution of NaOH (1N) (100 ml). The organic phase is dried over Na2SO4, filtered and then concentrated under reduced pressure. 0.58 g of product is obtained, in the form of a white powder. Yield 47%. Melting point 116° C. MH+: 171 (Tr: 1.03 min, condition 2).

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. washwashed 3 times with an aqueous solution of NaOH (1N) (100 ml)
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a86fd0b35bc34d6f9c669a22b5a5f379
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623893B2

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