(1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Base Information

Chemical Name:(1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
CAS No.:1548422-49-6
Molecular Formula:C₂₄H₂₈INO₅
Molecular Weight:537.395
Hs Code.:

Synonyms:(1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

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Chemical Property of (1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

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Technology Process of (1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

There total 3 articles about (1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 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: 76.0%

: 1548422-48-5
(S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)methyl]-8-iodo-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

: 1548422-49-6
(1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo4028775

Reference yield:

: 1548422-05-4
methyl 8-iodo-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

: 1548422-49-6
(1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 3-[{(1R,2R)-2-(dimethylamino)cyclohexyl}amino]-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide / dichloromethane / 24 h / 0 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 1 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; 3-[{(1R,2R)-2-(dimethylamino)cyclohexyl}amino]-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide; In methanol; dichloromethane; 1: |Mannich Aminomethylation;
DOI:10.1021/jo4028775

Reference yield:

: 651735-61-4
8-iodo-3,4-dihydronaphthalen-1(2H)-one

: 1548422-49-6
(1S,2S)-methyl 2-[(R)-[(tert-butoxycarbonyl)amino](phenyl)-methyl]-1-hydroxy-8-iodo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydride / mineral oil / 2 h / 70 °C / Inert atmosphere

2: 3-[{(1R,2R)-2-(dimethylamino)cyclohexyl}amino]-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide / dichloromethane / 24 h / 0 °C / Inert atmosphere

3: sodium tetrahydroborate / methanol / 1 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; 3-[{(1R,2R)-2-(dimethylamino)cyclohexyl}amino]-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide; sodium hydride; In methanol; dichloromethane; mineral oil; 2: |Mannich Aminomethylation;
DOI:10.1021/jo4028775