tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

Chemical Name:tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate
CAS No.:1432514-57-2
Molecular Formula:C₁₆H₂₃NO₃
Molecular Weight:277.364
Hs Code.:

Synonyms:tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Chemical Property of tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property:

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Technology Process of tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 2 articles about tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 878798-87-9
2-(tert-butoxycarbonyl)-1,2,3 ,4-tetrahydroisoquinoline-8-carboxylic acid

: 1432514-57-2
tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / tetrahydrofuran / 20 °C

2: tetrahydrofuran / 4 h / 0 °C

3: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane-THF / tetrahydrofuran / 0.83 h

With borane-THF; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran;

Reference yield:

: 878798-87-9
2-(tert-butoxycarbonyl)-1,2,3 ,4-tetrahydroisoquinoline-8-carboxylic acid

: 1432514-57-2
tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

: tert-butyl 8-[(1R)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 18 - 25 °C

2: tetrahydrofuran / 4 h / 0 °C

3: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran

4: ChiralPak AD-H / Resolution of racemate

With borane-THF; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran;

Reference yield: 43.0%

: 1432514-57-2
tert-butyl 8-[(1S)-1-hydroxyethyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

: 1607485-79-9
N-(2,4-dimethoxybenzyl)-5-fluoro-N-(6-fluoropyridin-2-yl)-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

: 1607485-80-2
(R)-tert-butyl 8-(1-(6-(N-(2,4-dimethoxybenzyl)-N-(6-fluoropyridin-2-yl)sulfamoyl)-5-fluoro-2-oxobenzo[d]oxazol-3(2H)-yl)ethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 3.16667h;
DOI:10.1016/j.bmcl.2017.04.040