Methanol → (5-Cyclohex-1-en-1-yl-4-hydroxy-7-isopropyl-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)[4-(tri-fluoromethyl)phenyl]methanone

HRID 1516738

반응식

HRID 1516738 반응식
N[C@@H]1C2C(=CC=CC=2)C[C@@H]1O.[C:12]1([C:18]2[C:27]([C:28](=[O:39])[C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)=[C:26]([CH:40]([CH3:42])[CH3:41])[CH:25]=[C:24]3[C:19]=2[C:20](=[O:45])[CH2:21][C:22]([CH3:44])([CH3:43])[O:23]3)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1.CO>O1CCCC1>[C:12]1([C:18]2[C:27]([C:28]([C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=3)=[O:39])=[C:26]([CH:40]([CH3:41])[CH3:42])[CH:25]=[C:24]3[C:19]=2[CH:20]([OH:45])[CH2:21][C:22]([CH3:43])([CH3:44])[O:23]3)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 690712705-Cyclohex-1-en-1-yl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

생성물 1

HCID 69068674(5-Cyclohex-1-en-1-yl-4-hydroxy-7-isopropyl-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)[4-(tri-fluoromethyl)phenyl]methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

80 μl (450 μmol) of borane/N,N-diethylaniline complex are added slowly to a solution of 2.51 mg (17 μmol) of (1R,2S)-1-aminoindan-2-ol in 2.6 ml of tetrahydrofuran. The mixture is then cooled to 0° C., and a solution of 53 mg (112 μmol) of 5-cyclohex-1-en-1-yl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one (Example 37A) in 2.6 ml of tetrahydrofuran is slowly added dropwise. The mixture is allowed to thaw slowly and stirred at room temperature overnight. Methanol is then added, and the solvent is removed under reduced pressure. The residue is taken up in ethyl acetate and washed in each case twice with 1 M hydrochloric acid and saturated sodium bicarbonate solution and once with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (mobile phase: cyclohexane→cyclohexane/ethyl acetate 20:1) and subsequent chiral HPLC (method 2) gives the target compound.

후처리

  1. customthe solvent is removed under reduced pressure
  2. washwashed in each case twice with 1 M hydrochloric acid and saturated sodium bicarbonate solution and once with saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by column chromatography on silica gel (mobile phase: cyclohexane→cyclohexane/ethyl acetate 20:1) and subsequent chiral HPLC (method 2)
  6. customgives the target compound

출처 및 근거

ORD 기록
ord-bc2f3a4335564d8e86c8ca055f0b4c41
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227511B2

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