(+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

Base Information

• Chemical Name: (+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole
• CAS No.: 171256-46-5
• Molecular Formula: C₁₉H₂₀N₂O₅S
• Molecular Weight: 388.444
• Mol file: 171256-46-5.mol

Synonyms:(+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

Chemical Property of (+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

There total 1 articles about (+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>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%

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9) → (+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole (171256-46-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo00124a055

Reference yield:

(+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole (171256-46-5) → (+)-(2R,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 3 h / Heating

2: n-Bu₃SnH, AIBN / chlorobenzene / 0.5 h

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; chlorobenzene;

DOI:10.1021/jo00124a055

Reference yield:

1,1'-Thiocarbonyldiimidazole (6160-65-2) + (+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole (171256-46-5) → (2S,3aR,8aS)-8-Benzenesulfonyl-2-(imidazole-1-carbothioyloxymethyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester (1025900-80-4)

Guidance literature:

In dichloromethane; for 3h; Heating;

DOI:10.1021/jo00124a055

upstream raw materials:

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate

Downstream raw materials:

(2S,3aR,8aS)-8-Benzenesulfonyl-2-(imidazole-1-carbothioyloxymethyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester