Triphenylphosphine → (R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one

HRID 1036514

반응식

HRID 1036514 반응식
[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.O[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C@:23]1([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]1)[CH:17]=[CH:16]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:29][C@@:23]1([C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([O:9][CH:6]4[CH2:5][CH2:4][CH:3]([C:2]([F:10])([F:11])[F:1])[CH2:8][CH2:7]4)[CH:14]=3)[CH:19]=2)[CH2:27][O:26][C:25](=[O:28])[NH:24]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27797654-(Trifluoromethyl)cyclohexan-1-olHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

생성물 1

HCID 67412717(R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a 40 mL vial, 4-trifluoromethyl-cyclohexanol (713.2 mg, 0.004241 mol) was diluted with tetrahydrofuran (19.0 mL), then (R)-4-(6-hydroxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (0.9462 g, 0.003890 mol) and triphenylphosphine (1.3031 g, 0.0049682 mol) were added. The mixture was stirred and then diisopropyl azodicarboxylate (0.91 mL, 0.0046 mol) was added. The reaction was stirred at room temperature for 38 h. The reaction mixture was concentrated in vacuo, taken up in DCM, adsorbed onto silica gel and chromatographed (0-100% EtOAc/Hexanes). Isolated was 223.5 mg (15%) of product as cis/trans mixture.

후처리

  1. stirringThe reaction was stirred at room temperature for 38 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customchromatographed (0-100% EtOAc/Hexanes)
  4. customIsolated

출처 및 근거

ORD 기록
ord-634278de22c040ddb4a64c9a3d4a7490
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546359B2

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