(+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole

Base Information

• Chemical Name: (+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole
• CAS No.: 112089-71-1
• Molecular Formula: C₂₄H₂₈N₂O₄
• Molecular Weight: 408.497

Synonyms:(+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole

Chemical Property of (+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole

Chemical Property:

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Technology Process of (+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole

There total 28 articles about (+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole 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: 66.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol (112243-83-1) → (+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole (112089-71-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 84h; Ambient temperature;

DOI:10.1021/jm00398a017

Reference yield:

N-(2-hydroxy-4-nitrophenyl)benzamide (38880-89-6) → (+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole (112089-71-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 94 percent / K₂CO₃ / n-Bu₄NI / acetone / 16 h / Heating

2: 90 percent / Na₂S₂O₄ / tetrahydrofuran; H₂O / 30 h / Heating

3: pyridine / tetrahydrofuran / 18 h / 22 °C

4: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C

5: CH₂Cl₂ / 10 h / 23 °C

6: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C

7: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C

8: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h

9: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating

10: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min

11: 83 percent / acetyl chloride / methanol / 2 h / 50 °C

12: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C

13: tetrahydrofuran / 20 h / 23 °C

With pyridine; lead(IV) acetate; hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; sodium dithionite; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; acetyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,2'-azobis(isobutyronitrile); tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ja00222a043

Reference yield:

N5-(Phenylsulfonyl)-5-amino-1-benzoyl-7-(benzyloxy)-3-methylindole (112764-63-3) → (+/-)-(1R*)-5-(benzyloxy)-3-<(tert-butyloxy)carbonyl>-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole (112089-71-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C

2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h

3: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating

4: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min

5: 83 percent / acetyl chloride / methanol / 2 h / 50 °C

6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C

7: tetrahydrofuran / 20 h / 23 °C

With sodium hydroxide; N-Bromosuccinimide; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; acetyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00222a043

upstream raw materials:

di-tert-butyl dicarbonate

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

3-nitro-4-chlorophenol

Downstream raw materials:

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

(R)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo<1,2-b:4,3-b'>dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

(R)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo<1,2-b:4,3-b'>dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

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