Triphenylphosphine → 4-[4-(2,2-Dimethyl-3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-pyran-4-carbonitrile

HRID 272922노트

반응식

HRID 272922 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:16][C:17]([CH3:26])([CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:18]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl.CO.C1COCC1>[CH3:16][C:17]([CH3:26])([CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:18][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 2681152,2-Dimethyl-3-(Pyrrolidin-1-Yl)Propan-1-OlHCID 5363146Diisopropyl azodicarboxylateHCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

생성물 1

HCID 598374034-[4-(2,2-Dimethyl-3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-pyran-4-carbonitrile수율 6.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21226129Dichloromethane methanol용매

실험 절차

4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (1.29 g, 6.4 mmol), 2,2-dimethyl-3-pyrrolidin-1-yl-propan-1-ol (0.8 g, 5.1 mmol), PPh3 (1.67 g, 6.4 mmol), THF (16 ml) and DIAD (1.25 ml, 6.4 mmol) were reacted together according to general procedure H. The crude material was subjected to chromatography on silica eluting with DCM:MeOH (98:2). The resulting solid was slurried in TBME:heptanes (1:2, 1 ml) to provide the title compound (120 mg, 5%) as a white solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.94 (d, 2H), 4.12-4.03 (m, 2H), 3.89 (td, 2H), 3.71 (s, 2H), 2.57 (br s, 4H), 2.47 (s, 2H), 2.15-1.99 (m, 4H), 1.70 (brs, 4H), 1.00 (s, 6H).

출처 및 근거

ORD 기록
ord-e8a55d31aec7448e9e2534b6c7af1421
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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