Triphenylphosphine → 1-(4-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)-N,N-dimethylmethanamine

HRID 272968ノート

反応式

HRID 272968 の反応式
[CH3:1][N:2]([CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[CH3:3].[CH:18]1([N:22]2[CH2:27][CH2:26][CH:25](O)[CH2:24][CH2:23]2)[CH2:21][CH2:20][CH2:19]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.ClCCl.CO.N>C1COCC1>[CH:18]1([N:22]2[CH2:27][CH2:26][CH:25]([O:17][C:14]3[CH:15]=[CH:16][C:11]([C:5]4([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]4)=[CH:12][CH:13]=3)[CH2:24][CH2:23]2)[CH2:21][CH2:20][CH2:19]1

参加物

7

反応物 5

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21584172Ammonia methanol dichloromethaneHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 581554161-Cyclobutylpiperidin-4-ol

生成物 1

HCID 598374051-(4-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)-N,N-dimethylmethanamine収率 11%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (0.75 g, 3.19 mmol), 1-cyclobutylpiperidin-4-ol (0.45 g, 2.90 mmol), PPh3 (0.84 g, 3.19 mmol), THF (10 ml) and DIAD (0.66 ml, 3.19 mmol) were reacted together similarly to general procedure C. The crude material was subjected to chromatography on silica gel eluting with dichloromethane:methanol:ammonia (98:2:0.2) to provide the title compound (114 mg, 11%) as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 1.71-1.77 (m, 4H), 1.85-1.90 (m, 4H), 1.94 (s, 6H), 1.99-2.06 (m, 4H), 2.12-2.16 (m, 2H), 2.20-2.28 (m, 2H), 2.45 (s, 2H), 2.58-2.70 (m, 2H), 2.79 (m, 1H), 3.46-3.53 (m, 2H), 3.72-3.75 (m, 2H), 4.39 (m, 1H), 6.91 (d, 2H), 7.26 (d, 2H). HRMS ESI+ m/z 373.2846 [MH]+.

出典と根拠

ORDレコード
ord-968e0f325d7345cfb4cea2264f173377
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

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