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

HRID 272968노트

반응식

HRID 272968 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

출처 및 근거

ORD 기록
ord-968e0f325d7345cfb4cea2264f173377
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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