Hydrochloric Acid → (4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

HRID 20055

반응식

HRID 20055 반응식
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.CSC.B.C1COCC1.[Br:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[O:38][C:37]([CH3:46])([C:42]([F:45])([F:44])[F:43])[CH2:36][C:35]2=[O:47].Cl>C1(C)C=CC=CC=1>[Br:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[O:38][C:37]([CH3:46])([C:42]([F:43])([F:45])[F:44])[CH2:36][C@H:35]2[OH:47]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 12423031(Dimethyl sulfide)trihydroboronHCID 673056026-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

생성물 1

HCID 67305384(4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a cooled (ice bath) solution of (s)-2-methyl-cbs-oxazaborolidine 1.0 M in toluene (100 μl, 100 μmol) was added borane-dimethyl sulfide 2.0 M in THF (500 μl, 1000 μmol). After stirred 15 min, a solution of 6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-one (309 mg, 1000 μmol) in toluene was added drop wise. The reaction was completed after stirring 9h at 0° C. 2N HCl was added slowly to quench the reaction. The resulted mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column to afford the title compound.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionThe resulted mixture was extracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel column

출처 및 근거

ORD 기록
ord-9e879ac3aa344099b227c59bf71a01e4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745484B2

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