Sodium Bicarbonate → 2-(4-Benzyl-morpholin-2-yl)-1,3-bis-(2-methoxy-phenyl)-propan-2-ol

HRID 30331노트

반응식

HRID 30331 반응식
C(O[C:4]([CH:6]1[O:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:5])C.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[CH2:23][Mg]Cl.[C:30](=[O:33])(O)[O-].[Na+]>O1CCCC1>[CH2:12]([N:8]1[CH2:9][CH2:10][O:11][CH:6]([C:4]([OH:5])([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:33][CH3:30])[CH2:23][C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[O:20][CH3:19])[CH2:7]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 15651196Ethyl 4-benzylmorpholine-2-carboxylateHCID 178489472HCID 178489472, 화합물

생성물 1

HCID 588548932-(4-Benzyl-morpholin-2-yl)-1,3-bis-(2-methoxy-phenyl)-propan-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Add a solution of 4-benzyl-morpholine-2-carboxylic acid ethyl ester (1.12 g, 4.49 mmol) in tetrahydrofuran (5 mL) to a stirred solution of 2-methoxybenzylmagnesium chloride (54 mL, 0.25M solution in tetrahydrofuran, commercially available from Rieke Metals) at −10° C. under nitrogen atmosphere. After 1 hour, add a saturated aqueous solution of sodium bicarbonate and extract with diethyl ether. Combine the organic layers and extract with brine, dry over magnesium sulfate, filter, and concentrate under reduced pressure to give a residue to be taken forward without further purification. MW 447.58; C28H33NO4; LCMS (12 minute method):m/z)=448.2 [M+H]+) RT 4.8 min.

후처리

  1. customat −10° C.
  2. extractionextract with diethyl ether
  3. extractionextract with brine
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customto be taken forward without further purification
  9. customLCMS (12 minute method)
  10. customRT 4.8 min.

출처 및 근거

ORD 기록
ord-8ef79c5512454b1b9d18808a10568d53
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423037B2

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