(4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol

Base Information

Chemical Name:(4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol
CAS No.:950479-60-4
Molecular Formula:C₁₈H₂₅NO₅S
Molecular Weight:367.466
Hs Code.:

Synonyms:(4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol

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Chemical Property of (4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol

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Technology Process of (4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol

There total 1 articles about (4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol 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: 78.0%

: 950479-56-8
(4S,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-6H-cyclopenta[c]pyridin-6-one

: 950479-60-4
(4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol

: (4S,6S,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; dichloromethane; at 20 ℃; for 0.25h;
DOI:10.1021/jo0709091

Reference yield:

: 950479-60-4
(4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol

: 950479-66-0
(4aR,6S,7S,7aS)-6-benzyloxy-7-methyl-2-(p-toluenesulfonyl)-octahydro-4H-cyclopenta[c]pyridin-4-one

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / H₂ / PtO₂ / tetrahydrofuran / 4.5 h / 20 °C

2: 82 percent / NaH; Bu₄NI / dimethylformamide / 7 h / 20 °C

3: 97 percent / aq. HCl / tetrahydrofuran / 2 h / 65 °C

4: 77 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

5: 81 percent / DBU / benzene / 0.5 h / 80 °C

With hydrogenchloride; oxalyl dichloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 4: Swern oxidation;
DOI:10.1021/jo0709091

Reference yield:

: 950479-60-4
(4S,6R,7S,7aS)-4-methoxymethoxy-7-methyl-2-(p-toluenesulfonyl)-1,2,3,4,7,7a-hexahydro-1H-cyclopenta[c]pyridin-6-ol

: (4aR,6S,7S,7aR)-6-benzyloxy-7-methyl-4-methylene-2-(p-toluenesulfonyl)-octahydro-1H-cyclopenta[c]pyridine

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / H₂ / PtO₂ / tetrahydrofuran / 4.5 h / 20 °C

2: 82 percent / NaH; Bu₄NI / dimethylformamide / 7 h / 20 °C

3: 97 percent / aq. HCl / tetrahydrofuran / 2 h / 65 °C

4: 77 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

5: 81 percent / DBU / benzene / 0.5 h / 80 °C

6: 17 percent / n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 4: Swern oxidation / 6: Wittig reaction;
DOI:10.1021/jo0709091