Methanol → HCID 66597382, compound

HRID 1518641Notes

Reaction equation

HRID 1518641 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:25])[NH:10]2)=[O:4].CO>O1CCCC1>[Br:1][CH2:2][C@@H:3]([C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:25])[NH:10]2)[OH:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 86662509HCID 86662509, compound

Product 1

HCID 66597382HCID 66597382, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

Under an argon flow, 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (7.15 g, 17.8 mmol) was suspended in dehydrated tetrahydrofuran (40 mL), the CBS catalyst (493 mg) was added thereto, and the reaction mixture was stirred at −20° C. for 40 minutes. After adding dropwise a 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (21.4 mL) at the same temperature, the mixture was warmed gradually to 0° C. After adding methanol (20 mL) dropwise, insoluble matter was filtered off and washed with tetrahydrofuran. The filtrate and the washing were mixed and concentrated under reduced pressure. To the residue was added purified water (100 mL) and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration and washed with purified water. The precipitate was further suspension-washed with ethyl acetate (200 mL), collected by filtration, and dried under reduced pressure to obtain 5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (3.06 g).

Workup

  1. temperaturethe mixture was warmed gradually to 0° C
  2. filtrationinsoluble matter was filtered off
  3. washwashed with tetrahydrofuran
  4. additionThe filtrate and the washing were mixed
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added
  7. custompurified water (100 mL)
  8. stirringthe mixture was stirred at room temperature overnight
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with purified water
  11. washThe precipitate was further suspension-washed with ethyl acetate (200 mL)
  12. filtrationcollected by filtration
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-5f1a7fe1eb294a49827aeb8e506e1f39
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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