Benzylamine → 2-Benzyl-2,3-dihydro-1H-isoindole

HRID 1486490노트

반응식

HRID 1486490 반응식
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1[CH2:13][CH2:12][CH2:11][CH2:10]1>C(N(CC)CC)C>[CH2:1]([N:8]1[CH2:4][C:3]2[C:11](=[CH:12][CH:13]=[CH:1][CH:2]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 7504BenzylamineHCID 8028Tetrahydrofuran

생성물 1

HCID 14027062-Benzyl-2,3-dihydro-1H-isoindole

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

In Scheme 3, the bis-bromomethyl benzoic acid ester (26) is reacted with benzylamine in a polar aprotic solvent such as tetrahydrofuran (THF) in the presence of a non-interfering base such as triethylamine to give the N-benzyl dihydroisoindole intermediate (27). The ester group in intermediate (27) is then reduced to the corresponding alcohol using lithium aluminium hydride in THF to give the hydroxymethyldihydroisoindole intermediate (28). Debenzylation of the hydroxymethyldihydroisoindole intermediate (28) is then carried out by hydrogenation over palladium on charcoal catalyst in an alcohol (e.g. ethanol) solvent at a mildly elevated temperature (e.g. up to about 50°) to give the intermediate (29). Intermediate (29) is then converted to intermediate (20) by reaction with a reagent suitable for introducing a benzyloxycarbonyl (“Z”) group onto the nitrogen atom of the dihydroisoindole ring. For example, the intermediate (29) can be reacted with benzyl chloroformate in a polar non-protic solvent such as THF in the presence of a non-interfering base such as triethylamine to give intermediate (20).

출처 및 근거

ORD 기록
ord-88e2d13603cb4dfd9a61c1da3db3cd7b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428439B2

반응 노트

불러오는 중…