Methanol → HCID 86602718、化合物

HRID 1178859ノート

反応式

HRID 1178859 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 86602718HCID 86602718、化合物収率 62%

試薬・触媒・溶媒 1

HCID 11026Titanium isopropoxide触媒

反応条件

温度
80 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-d32c2ab6716b4a8c990588e91b49b3fe
出典データセット
uspto-grants-2007_10
特許番号
US07276631B2

反応ノート

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