{3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester
• CAS No.: 760968-85-2
• Molecular Formula: C₃₂H₃₈N₂O₆S
• Molecular Weight: 578.73
• Mol file: 760968-85-2.mol

Synonyms:{3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester

Chemical Property of {3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester

There total 13 articles about {3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester 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: 93.0%

{3-[6-benzyloxy-3-formyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester (760968-82-9) → {3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester (760968-85-2)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 40 ℃; for 15h;

DOI:10.1055/s-2004-829085

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → {3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester (760968-85-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / 4-(dimethylamino)pyridine / acetonitrile / 2 h / 23 °C

2: 100 percent / DIBALH / tetrahydrofuran / 1 h / -78 °C

3: 99 percent / toluene / 13 h / 100 °C

4: 76 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

5: 92 percent / MnO₂ / CH₂Cl₂ / 12 h / 23 °C

6: 98 percent / BnNEt₃Cl; Na₂CO₃ / CH₂Cl₂ / 18 h / 20 °C

7: 93 percent / NaBH₄; CeCl₃*7H₂O / methanol / 15 h / 40 °C

With dmap; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; N-benzyl-N,N,N-triethylammonium chloride; diisobutylaluminium hydride; sodium carbonate; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1055/s-2004-829085

Reference yield:

2-amino-5-hydroxybenzoic acid (394-31-0) → {3-[6-benzyloxy-3-hydroxymethyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester (760968-85-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / SO₂Cl / Heating

2: 97 percent / pyridine / ethyl acetate

3: 93 percent / NaH / dimethylformamide / 20 °C

4: 100 percent / LiBH₄ / tetrahydrofuran / 20 °C

5: 80 percent / pyridinium dichromate / CH₂Cl₂ / 20 °C

6: 98 percent / BnNEt₃Cl; Na₂CO₃ / CH₂Cl₂ / 18 h / 20 °C

7: 93 percent / NaBH₄; CeCl₃*7H₂O / methanol / 15 h / 40 °C

With pyridine; sodium tetrahydroborate; dipyridinium dichromate; lithium borohydride; sulfuryl dichloride; cerium(III) chloride; N-benzyl-N,N,N-triethylammonium chloride; sodium hydride; sodium carbonate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-829085

upstream raw materials:

{3-[6-benzyloxy-3-formyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

2-amino-5-hydroxybenzoic acid

methyl 2-amino-5-hydroxybenzoate

Downstream raw materials:

{3-[6-benzyloxy-3-methylene-4-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester

{3-[6-benzyloxy-4-hydroxy-3-methylene-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester