tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

• Chemical Name: tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS No.: 1204765-84-3
• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.337
• Mol file: 1204765-84-3.mol

Synonyms:tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property of tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

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MSDS Files:

SDS file from LookChem

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Technology Process of tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 2 articles about tert-butyl 8-(hydroxymethyl)-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: 95.0%

2-(tert-butoxycarbonyl)-1,2,3 ,4-tetrahydroisoquinoline-8-carboxylic acid (878798-87-9) → tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1204765-84-3)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 0 - 50 ℃; for 38h;

Reference yield:

8-bromo-isoquinoline (63927-22-0) → tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1204765-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium cyanoborohydride; methanol / 0.17 h / 0 °C

1.2: 5 h / 0 °C

2.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

3.1: triethylamine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 4 h / 70 °C / 2068.65 Torr

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

With methanol; lithium aluminium tetrahydride; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

tert-butyl 8-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1204765-84-3) + N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydro-1,3-benzoxazole-6-sulfonamide (1432514-64-1) → tert-butyl 8-({6-[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)sulfamoyl]-5-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl}methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1432514-65-2)

Guidance literature:

With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.5h;

upstream raw materials:

2-(tert-butoxycarbonyl)-1,2,3 ,4-tetrahydroisoquinoline-8-carboxylic acid

8-bromo-isoquinoline

Downstream raw materials:

tert-butyl 8-({6-[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)sulfamoyl]-5-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl}methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

C₃₃H₃₅N₅O₈S₂

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