5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole

Base Information

• Chemical Name: 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole
• CAS No.: 122745-39-5
• Molecular Formula: C₂₅H₂₇NO₄
• Molecular Weight: 405.494
• Mol file: 122745-39-5.mol

Synonyms:5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole

Chemical Property of 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole

There total 23 articles about 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole 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%

5-(Benzyloxy)-3-(tert-butyloxycarbonyl)-1-<(tetrahydropyranyloxy)methyl>-1,2-dihydro-3H-benzindole (139976-01-5) → 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole (122745-39-5)

Guidance literature:

With Amberlyst 15; In methanol; at 45 ℃; for 6h;

DOI:10.1021/jo00036a023

Reference yield: 80.0%

5-(Benzyloxy)-3-(tert-butyloxycarbonyl)-1-<<(2',2',6',6'-tetramethylpiperidino)oxy>methyl>-1,2-dihydro-3H-benzindole (161646-55-5) → 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole (122745-39-5)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 70 ℃; for 2h;

DOI:10.1021/jo00110a034

Reference yield:

N-(tert-butyloxycarbonyl)-4-(benzyloxy)-2-naphthylamine (122745-36-2) → 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole (122745-39-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / N-iodosuccinimide, H₂SO₄ / tetrahydrofuran; methanol / 3 h / -78 °C

2: 95 percent / NaH / dimethylformamide / 1.) 0 deg C, 45 min, 2.) 25 deg C, 3 h

3: 90 percent / Bu₃SnH / benzene / 1 h / 70 °C

4: 80 percent / Zn, aq. CH₃COOH / tetrahydrofuran / 2 h / 70 °C

With N-iodo-succinimide; sulfuric acid; tri-n-butyl-tin hydride; sodium hydride; acetic acid; zinc; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00110a034

upstream raw materials:

5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-methylidene-1,2-dihydro-3H-benzindole

5-(Benzyloxy)-3-(tert-butyloxycarbonyl)-1-<(tetrahydropyranyloxy)methyl>-1,2-dihydro-3H-benzindole

5-(Benzyloxy)-3-(tert-butyloxycarbonyl)-1-<<(2',2',6',6'-tetramethylpiperidino)oxy>methyl>-1,2-dihydro-3H-benzindole

N-(tert-butyloxycarbonyl)-4-(benzyloxy)-2-naphthylamine

Downstream raw materials:

tert-butyl (S)-1-(chloromethyl)-5-((4-methylpiperazine-1-carbonyl)oxy)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

(+)-CBI-CDPI2

5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-benzindole

(-)-(1R)-5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole