1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S)-

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Chemical Name:1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S)-
CAS No.:878999-43-0
Molecular Formula:C27H43NO3
Molecular Weight:429.643
Hs Code.:

Synonyms:

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Chemical Property of 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S)-

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Technology Process of 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S)-

There total 11 articles about 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S)- 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: 98.0%

: 878999-41-8
(S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-tetradecyl]-2-methyl-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

: 878999-43-0
(S)-4-((R)-1-Hydroxy-tetradecyl)-2-methyl-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 6h;
DOI:10.1021/ol052839v

Reference yield:

: 878999-34-9
(1-(S)-methyl-allyl)carbamic acid benzyl ester

: 878999-43-0
(S)-4-((R)-1-Hydroxy-tetradecyl)-2-methyl-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / NaH / dimethylformamide / 21 h / 0 - 20 °C

2: 76 percent / (N,N'-Mes₂-imidazolidin-2-yl)Ru=(CH-C₆H₄-2-O-iPr)Cl₂ / CH₂Cl₂ / 25 h / 20 °C

3: 98 percent / Bu₄NF / tetrahydrofuran / 6 h / 0 °C

With tetrabutyl ammonium fluoride; sodium hydride; Hoveyda-Grubbs 2nd-generation catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol052839v

Reference yield:

: (E)-2-Methyl-hexadec-2-en-1-ol

: 878999-43-0
(S)-4-((R)-1-Hydroxy-tetradecyl)-2-methyl-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 64 percent / D-DIPT; Ti(OiPr)4; t-BuOOH / decane; CH₂Cl₂ / 16 h / -20 °C

2: 86 percent / n-BuLi; iPr₂NH / hexane; tetrahydrofuran / 18 h / 20 °C

3: 40 percent / N-bromosuccinimide; PPh₃ / CH₂Cl₂ / 8 h / 0 °C

4: 71 percent / imidazole / dimethylformamide / 22 h / 35 °C

5: 73 percent / NaH / dimethylformamide / 21 h / 0 - 20 °C

6: 76 percent / (N,N'-Mes₂-imidazolidin-2-yl)Ru=(CH-C₆H₄-2-O-iPr)Cl₂ / CH₂Cl₂ / 25 h / 20 °C

7: 98 percent / Bu₄NF / tetrahydrofuran / 6 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; D-(-)-diisopropyl tartrate; diisopropylamine; triphenylphosphine; Hoveyda-Grubbs 2nd-generation catalyst; In tetrahydrofuran; decane; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol052839v