(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole

Base Information

Chemical Name:(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole
CAS No.:237404-30-7
Molecular Formula:C₁₅H₁₉NO₄S
Molecular Weight:309.386
Hs Code.:

(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopenta<c>pyrrole

Synonyms:(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole

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Chemical Property of (1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole

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Technology Process of (1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole

There total 6 articles about (1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole 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: 69.0%

: 237404-29-4
(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-hydroxymethylhexahydro-cyclopentapyrrole

: 237404-30-7
(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole

Guidance literature:: With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; for 18h; Ambient temperature;
DOI:10.1016/S0040-4020(99)00425-1

Reference yield:

: 5-(dimethylphenylsilyl)-pent-3-en-1-ol

: 237404-30-7
(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N, DMAP / CH₂Cl₂ / 4 h / 0 °C

2: NaI / acetone / 2 h / Heating

3: 1.) t-BuLi, 2.) CuI/n-Bu₃P / 1.) pentane, Et₂O, -78 deg C, 10 min, room temperature, 60 min, 2.) Et₂O, -40 deg C, 10 min, -78 deg C, 40 min, 3.) THF, Et₂O, -78 deg C, 60 min

4: 65 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

5: 79 percent / peracetic acid, Hg(OAc)2 / acetic acid; ethyl acetate / 3 h / Ambient temperature

6: 69 percent / NaIO₄, aq. RuCl₃ / CCl₄; acetonitrile / 18 h / Ambient temperature

With peracetic acid; dmap; ruthenium trichloride; sodium periodate; copper(l) iodide; tributylphosphine; boron trifluoride diethyl etherate; mercury(II) diacetate; tert.-butyl lithium; triethylamine; sodium iodide; In tetrachloromethane; dichloromethane; acetic acid; ethyl acetate; acetone; acetonitrile;
DOI:10.1016/S0040-4020(99)00425-1

Reference yield:

: 1-iodo-5-(dimethylphenylsilyl)-pent-3-ene

: 237404-30-7
(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-carboxylic acid hexahydro-cyclopentapyrrole

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) t-BuLi, 2.) CuI/n-Bu₃P / 1.) pentane, Et₂O, -78 deg C, 10 min, room temperature, 60 min, 2.) Et₂O, -40 deg C, 10 min, -78 deg C, 40 min, 3.) THF, Et₂O, -78 deg C, 60 min

2: 65 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

3: 79 percent / peracetic acid, Hg(OAc)2 / acetic acid; ethyl acetate / 3 h / Ambient temperature

4: 69 percent / NaIO₄, aq. RuCl₃ / CCl₄; acetonitrile / 18 h / Ambient temperature

With peracetic acid; ruthenium trichloride; sodium periodate; copper(l) iodide; tributylphosphine; boron trifluoride diethyl etherate; mercury(II) diacetate; tert.-butyl lithium; In tetrachloromethane; dichloromethane; acetic acid; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(99)00425-1