(1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester
CAS No.:211426-31-2
Molecular Formula:C₁₈H₂₃NO₂
Molecular Weight:285.386
Hs Code.:

Synonyms:(1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

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Chemical Property of (1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

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Technology Process of (1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

There total 11 articles about (1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 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%

: 211426-30-1
(S)-2-(3-Phenyl-prop-2-ynyl)-5-phenylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 211426-31-2
(1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃;
DOI:10.1016/S0040-4039(98)00958-7

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 211426-31-2
(1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaOH / 2-methyl-propan-2-ol

2: DCC, HOBt, Et₃N / CH₂Cl₂

3: LiAlH₄ / diethyl ether / -40 °C

4: LiCl, Et(iPr)2N / acetonitrile

5: 89 percent / DIBAL-H, BF₃*Et₂O / CH₂Cl₂ / -78 °C

With sodium hydroxide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium chloride; In diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4039(98)01804-8

Reference yield:

: 108963-96-8
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

: 211426-31-2
(1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / DIBAL-H / CH₂Cl₂; tetrahydrofuran / -78 °C

2: 81 percent / TsOH*H₂O

3: 73 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4: 90 percent / tetrahydrofuran / -78 °C

5: 77 percent / DMAP / CH₂Cl₂

6: 76 percent / Bu₃SnH, AIBN / toluene / 80 °C

7: 80 percent / TsOH*H₂O / CH₂Cl₂

8: 76 percent / Bu₃SnH, AIBN / toluene / 110 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/S0040-4039(98)00958-7