Trifluoroacetic acid → HCID 71281323, 화합물

HRID 1039014

반응식

HRID 1039014 반응식
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3][NH:2]1.CO[C:14]1[CH:19]=[CH:18][CH:17]=[C:16](OC)[CH:15]=1.FC(F)(F)C(O)=O>C(O)(=O)C>[C:14]1([C:9]2[C:8]([OH:11])=[CH:7][CH:6]=[C:5]3[C:10]=2[CH2:1][NH:2][CH2:3][CH2:4]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 90251,3-DimethoxybenzeneHCID 4192681,2,3,4-Tetrahydroisoquinolin-7-ol

생성물 1

HCID 71281323HCID 71281323, 화합물

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Scheme 1 (FIG. 1): Protection of the hydroxyl group in vanillin with benzyl bromide yielded aldehyde 1 is shown in Scheme 1. Henry reaction between aldehyde 1 and nitromethane gave nitrostyrene 2. Reduction of compound 2 with lithium aluminum hydride in tetrahydrofuran (THF) afforded amine 3. The reaction of amine 3 with an excess amount of methyl formate provided formamide 4. Cyclization of amide 4 using phosphorus oxychloride (POCl3) via Bischler-Napieralski reaction obtained 3,4-dihydroisoquinoline 5. Alkylation of compound 5 with iodopropane followed by NaBH4 reduction produced tetrahydroisoquinoline 6 in high yield. Catalytic hydrogenation over Pd/C removed the protective groups of 6 to afford 1,2,3,4-tetrahydroisoquinolin-7-ol 7 in quantitative yield. Treatment of compound 7 with Pb(OAc)4 in acetic acid followed by acid-catalyzed aromatic substitution with 1,3-dimethoxybenzene using trifluoroacetic acid (TFA) furnished 8-phenyl-tetrahydroisoquinolin-7-ol 8.

후처리

  1. customCatalytic hydrogenation over Pd/C removed the protective groups of 6
  2. customto afford 1,2,3,4-tetrahydroisoquinolin-7-ol 7 in quantitative yield

출처 및 근거

ORD 기록
ord-0feffa73d5f647bc8258b3fb1df8f72a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552028B2

연결된 노트

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