4-bromo-N,N-diethyl-2-[(2R)-2-hydroxypropyl]benzamide → (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one

HRID 2175778

반응식

HRID 2175778 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([C:6](N(CC)CC)=[O:7])=[C:4]([CH2:15][C@H:16]([OH:18])[CH3:17])[CH:3]=1>Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:13][CH:14]=1)[C:6](=[O:7])[O:18][C@H:16]([CH3:17])[CH2:15]2

참가 물질

4

반응물 1

HCID 866930334-bromo-N,N-diethyl-2-[(2R)-2-hydroxypropyl]benzamide

생성물 1

HCID 71270763(3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 4-bromo-N,N-diethyl-2-[(2R)-2-hydroxypropyl]benzamide (12.2 g, 38.8 mmol) dissolved in 4N HCl in dioxane (200 mL) was stirred at room temperature and monitored by TLC. After 3 days the reaction was partitioned between EtOAc (300 mL) and water (300 mL). The aqueous phase was further extracted with EtOAc (2×250 mL). The combined organic layers were then washed with water (200 mL), brine (200 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was then purified via MPLC (15-30% EtOAc/Hexane) to afford (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one: 1H NMR (500 MHz; CDCl3): 7.98 (d, J=8.2 Hz, 1H), 7.56 (dd, J=1.5, 8.2 Hz, 1H), 7.45 (s, 1H), 4.71 (m, 1H), 2.94 (m, 2H), 1.55 (d, J=6.3 Hz, 3H); LC-MS: (M+1)+ 241.

후처리

  1. customAfter 3 days the reaction was partitioned between EtOAc (300 mL) and water (300 mL)
  2. extractionThe aqueous phase was further extracted with EtOAc (2×250 mL)
  3. washThe combined organic layers were then washed with water (200 mL), brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was then purified via MPLC (15-30% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-10d94f4369b243c4a4a984d2df7137e7
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062070B2

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