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

HRID 30322ノート

反応式

HRID 30322 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-48cfe3673d67467abfa9814c6d2feaf2
出典データセット
uspto-grants-2008_09
特許番号
US07423037B2

反応ノート

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