(2R)-2-(Methoxymethyl)pyrrolidine → HCID 11611411, 화합물

HRID 272870

반응식

HRID 272870 반응식
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH:22]=O)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:24][O:25][CH2:26][C@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[CH3:24][O:25][CH2:26][C@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:22][C:16]1([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:15][CH:14]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

참가 물질

5

반응물 2

HCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 598374274-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde

생성물 1

HCID 11611411HCID 11611411, 화합물수율 59.4%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 702Ethanol용매

실험 절차

4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (500 mg, 1.575 mmol), (R)-2-(methoxymethyl)pyrrolidine (347 mg, 4.21 mmol), absolute ethanol (20 ml), activated 3 Å molecular sieves (500 mg), titanium (IV) isopropoxide (2.33 ml, 7.88 mmol) and STAB (2.84 g, 13.4 mmol) were reacted in accordance with the general procedure D. The isolated waxy solid was purified by column chromatography on silica eluting with DCM:MeOH:NH3 95:14:1 to give the title compound as a viscous pale yellow oil (390 mg, 59%). 1H NMR (400 MHz, CDCl3) δ7.18 (d, 2H), 6.86 (d, 2H), 4.02 (t, 2H), 3.85-3.69 (m, 2H), 3.59 (td, 1H), 3.45 (td, 1H), 3.27 (s, 3H), 3.10 (dd, 1H), 3.02 (dd, 1H), 2.94 (d, 1H), 2.63 (t, 2H), 2.58-2.45 (m, 6H), 2.39 (m, 1H), 2.21 (m, 1H), 2.07-1.67 (m, 11H), 1.57-1.33 (m, 3H).

후처리

  1. customThe isolated waxy solid was purified by column chromatography on silica eluting with DCM:MeOH:NH3 95:14:1

출처 및 근거

ORD 기록
ord-3db96ad8a53f460e91014ce84ac42750
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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