(2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl ester
• CAS No.: 300676-93-1
• Molecular Formula: C₂₄H₃₀N₂O₄
• Molecular Weight: 410.513
• Mol file: 300676-93-1.mol

Synonyms:(2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl ester

Chemical Property of (2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl ester

There total 9 articles about (2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl 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: 83.0%

methylamine (74-89-5) + 3-hydroxy-6-methoxy-4a-methyl-1-vinyl-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]indole-9-carboxylic acid benzyl ester (300676-90-8) → (2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl ester (300676-93-1)

Guidance literature:

With sodium cyanoborohydride; In methanol; at 90 ℃; for 12h;

DOI:10.1021/ol006065o

Reference yield:

(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one (221015-46-9) → (2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl ester (300676-93-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / H₂ / Pd-C / ethyl acetate

2: 70 percent / LHMDS; HMPA / tetrahydrofuran

3: 70 percent / pyridine; H₂O / 2.5 h / Heating

4: LiAlH₄ / tetrahydrofuran / 0 °C

5: aq. K₂CO₃

6: 89 percent / TBAF / tetrahydrofuran

7: 97 percent / Zn; AcOH / ethanol / Heating

8: 83 percent / NaBH₃CN / methanol / 12 h / 90 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium cyanoborohydride; potassium carbonate; acetic acid; lithium hexamethyldisilazane; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; water; ethyl acetate; 1: Hydrogenation / 2: Methylation / 3: <3,3>-sigmatropic rearrangement; cyclization / 4: Reduction / 5: Condensation / 6: Hydrolysis / 7: reductive cleavage / 8: Ring cleavage;

DOI:10.1021/ol006065o

Reference yield:

4-methoxyphenylhydrazine hydrochloride (19501-58-7) → (2R,3S)-2-((S)-1-Hydroxy-allyl)-5-methoxy-3-methyl-3-(2-methylamino-ethyl)-2,3-dihydro-indole-1-carboxylic acid benzyl ester (300676-93-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / pyridine; H₂O / 2.5 h / Heating

2: LiAlH₄ / tetrahydrofuran / 0 °C

3: aq. K₂CO₃

4: 89 percent / TBAF / tetrahydrofuran

5: 97 percent / Zn; AcOH / ethanol / Heating

6: 83 percent / NaBH₃CN / methanol / 12 h / 90 °C

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium cyanoborohydride; potassium carbonate; acetic acid; zinc; In tetrahydrofuran; pyridine; methanol; ethanol; water; 1: <3,3>-sigmatropic rearrangement; cyclization / 2: Reduction / 3: Condensation / 4: Hydrolysis / 5: reductive cleavage / 6: Ring cleavage;

DOI:10.1021/ol006065o

upstream raw materials:

methylamine

3-hydroxy-6-methoxy-4a-methyl-1-vinyl-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]indole-9-carboxylic acid benzyl ester

4-methoxyphenylhydrazine hydrochloride

(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one

Downstream raw materials:

(-)-esermethole

5-methoxy-1,3a-dimethyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid benzyl ester

2-acetoxy-3-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

(2R,3S)-3-[2-(tert-Butoxycarbonyl-methyl-amino)-ethyl]-2-((S)-1-hydroxy-allyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester