17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan

Base Information

Chemical Name:17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan
CAS No.:221103-40-8
Molecular Formula:C₄₂H₄₂N₂O₆S
Molecular Weight:702.871
Hs Code.:

Synonyms:17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan

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Chemical Property of 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan

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Technology Process of 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan

There total 7 articles about 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan 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: 86.0%

: 98-59-9
p-toluenesulfonyl chloride

: 221103-39-5
17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-(2-hydroxyethyl)-6,7-2',3'-indolomorphinan

: 221103-40-8
17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan

Guidance literature:: With potassium trimethylsilonate; In toluene; at 0 ℃; for 1h;
DOI:10.1002/(SICI)1099-1344(199901)42:1<43::AID-JLCR165>3.0.CO;2-2

Reference yield:

: 2216-92-4
N-phenylglycine ethyl ester

: 221103-40-8
17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan

Guidance literature:: Multi-step reaction with 6 steps

1: NaNO₂

2: Zn; AcOH

3: 64 percent / acetic acid / 5.5 h / 105 °C

4: 96 percent / potassium carbonate / dimethylformamide / 6 h / 95 °C

5: 89 percent / LiAlH₄ / tetrahydrofuran; toluene / 2 h / 0 °C

6: 86 percent / potassium trimethylsilanolate / toluene / 1 h / 0 °C

With lithium aluminium tetrahydride; potassium trimethylsilonate; potassium carbonate; acetic acid; zinc; sodium nitrite; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; toluene; 1: Nitrosation / 2: Reduction / 3: Fischer indole cyclization / 4: Etherification / 5: Reduction / 6: Tosylation;
DOI:10.1002/(SICI)1099-1344(199901)42:1<43::AID-JLCR165>3.0.CO;2-2

Reference yield:

: 50270-61-6
N-ethoxycarbonylmethyl-N-nitrosoaniline

: 221103-40-8
17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-1'-[2-(p-tolylsulfonyl)oxyethyl]-6,7-2',3'-indolomorphinan

Guidance literature:: Multi-step reaction with 5 steps

1: Zn; AcOH

2: 64 percent / acetic acid / 5.5 h / 105 °C

3: 96 percent / potassium carbonate / dimethylformamide / 6 h / 95 °C

4: 89 percent / LiAlH₄ / tetrahydrofuran; toluene / 2 h / 0 °C

5: 86 percent / potassium trimethylsilanolate / toluene / 1 h / 0 °C

With lithium aluminium tetrahydride; potassium trimethylsilonate; potassium carbonate; acetic acid; zinc; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; toluene; 1: Reduction / 2: Fischer indole cyclization / 3: Etherification / 4: Reduction / 5: Tosylation;
DOI:10.1002/(SICI)1099-1344(199901)42:1<43::AID-JLCR165>3.0.CO;2-2