Hydrochloric Acid → (4-Benzylmorpholin-2-yl)(cyclopropyl)methanol

HRID 30322노트

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HRID 30322 반응식
B.C1COCC1.[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH:20]([CH:22]2[CH2:24][CH2:23]2)[OH:21])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.CO>[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH:20]([CH:22]2[CH2:24][CH2:23]2)[OH:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 597892904-Benzyl-2-(cyclopropyl(hydroxy)methyl)morpholin-3-one

생성물 1

HCID 59789293(4-Benzylmorpholin-2-yl)(cyclopropyl)methanol수율 61%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

Borane-THF complex (1M solution in THF, 30 mL, 30 mmol, 4.1 eq) is added slowly to a solution of 75 (1.9 g, 7.3 mmol) in THF (100 mL). The reaction is heated to 60° C. After 24 hours MeOH and hydrochloric acid (2M, excess) are added and the resulting mixture heated for one hour at the same temperature. After careful addition of saturated NaHCO3 solution and EtOAc the aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried over magnesium sulphate and the solvent is removed in vacuo. Purification by ion exchange chromatography gives 76 (1.1 g, 61%). MW 247.34; C15H21NO2; LCMS (6 min method) m/z 248 [M+H]+, RT 2.48 min

후처리

  1. temperaturethe resulting mixture heated for one hour at the same temperature
  2. extractionis extracted with EtOAc
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is removed in vacuo
  6. customPurification by ion exchange chromatography

출처 및 근거

ORD 기록
ord-48cfe3673d67467abfa9814c6d2feaf2
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423037B2

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