Methanol → HCID 86602718, 화합물

HRID 1178859노트

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HRID 1178859 반응식
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1.[CH3:31][OH:32].[BH4-].[Na+].[OH2:35].[CH3:36][NH2:37]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]([F:30])([F:29])[C:31]([OH:35])=[O:32].[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][CH:11]([NH:37][CH3:36])[CH2:10]1

참가 물질

7

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HCID 887MethanolHCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 219731213-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclohexanone

생성물 1

HCID 86602718HCID 86602718, 화합물수율 62%

시약·촉매·용매 1

HCID 11026Titanium isopropoxide촉매

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온도
80 °C

실험 절차

To a solution of 3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclohexanone (10 mg) in methylamine (2.0 M solution in THF, 0.11 mL) at room temperature was added titanium(IV) isopropoxide (0.02 mL) and the resulting solution was heated at 80° C. in a sealed vial for 1.5 h. The solution was cooled to room temperature, 0.1 mL methanol was added followed by sodium borohydride (4.4 mg), and the resulting suspension was stirred at room temperature for 2 h. H2O was added to quench the reaction and the mixture was extracted with dichloromethane 3 times. The combined organic layers were concentrated and residue was purified by preparative HPLC to give the title compound (8 mg, 62% yield). 1H NMR (500 MHz, CD3OD) δ 1.39 (1H, m), 1.56 (1H, m), 1.72 (1H, m), 1.88 (1H, m), 2.14 (1H, m), 2.39 (1H, m), 2.61 (1H, m), 2.70 (3H, d, J=25 Hz), 2.71 (1H, m), 3.44 (1H, d, J=5 Hz), 3.79 (2H, dd, J=10, 60 Hz), 4.49-4.60 (2H, m), 7.21-7.28 (1H, m), 7.33 (1H, t, J=8 Hz), 7.38-7.46 (3H, m), 7.65 (1H, s), 7.72 (1H, s), 7.82 (1H, d, J=10 Hz). HPLC purity (retention time): 95% (2.05 min, method C). MS: 446.49 (MH+).

후처리

  1. temperatureThe solution was cooled to room temperature
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with dichloromethane 3 times
  5. concentrationThe combined organic layers were concentrated
  6. customresidue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-d32c2ab6716b4a8c990588e91b49b3fe
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276631B2

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