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

HRID 20055

反応式

HRID 20055 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9e879ac3aa344099b227c59bf71a01e4
出典データセット
uspto-grants-2010_06
特許番号
US07745484B2

関連ノート

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