1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S,3R,4R)-

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Chemical Name:1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S,3R,4R)-
CAS No.:878999-45-2
Molecular Formula:C27H45NO4
Molecular Weight:447.659
Hs Code.:

Synonyms:

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Chemical Property of 1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S,3R,4R)-

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Technology Process of 1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S,3R,4R)-

There total 11 articles about 1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-[(1R)-1-hydroxytetradecyl]-2-methyl-, phenylmethyl ester, (2S,3R,4R)- 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%

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

: 878999-45-2
(2S,3R,4R)-3-Hydroxy-4-((R)-1-hydroxy-tetradecyl)-2-methyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: (S)-4-((R)-1-Hydroxy-tetradecyl)-2-methyl-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; at 20 ℃; for 2.5h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 2h;
DOI:10.1021/ol052839v

Reference yield:

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

: 878999-45-2
(2S,3R,4R)-3-Hydroxy-4-((R)-1-hydroxy-tetradecyl)-2-methyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 73 percent / NaH / dimethylformamide / 21 h / 0 - 20 °C

2.1: 76 percent / (N,N'-Mes₂-imidazolidin-2-yl)Ru=(CH-C₆H₄-2-O-iPr)Cl₂ / CH₂Cl₂ / 25 h / 20 °C

3.1: 98 percent / Bu₄NF / tetrahydrofuran / 6 h / 0 °C

4.1: BH₃*Me₂S / diethyl ether; tetrahydrofuran / 2.5 h / 20 °C

4.2: 76 percent / H₂O₂; NaOH / diethyl ether; tetrahydrofuran / 2 h / 0 - 20 °C

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

Reference yield:

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

: 878999-45-2
(2S,3R,4R)-3-Hydroxy-4-((R)-1-hydroxy-tetradecyl)-2-methyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 64 percent / D-DIPT; Ti(OiPr)4; t-BuOOH / decane; CH₂Cl₂ / 16 h / -20 °C

2.1: 86 percent / n-BuLi; iPr₂NH / hexane; tetrahydrofuran / 18 h / 20 °C

3.1: 40 percent / N-bromosuccinimide; PPh₃ / CH₂Cl₂ / 8 h / 0 °C

4.1: 71 percent / imidazole / dimethylformamide / 22 h / 35 °C

5.1: 73 percent / NaH / dimethylformamide / 21 h / 0 - 20 °C

6.1: 76 percent / (N,N'-Mes₂-imidazolidin-2-yl)Ru=(CH-C₆H₄-2-O-iPr)Cl₂ / CH₂Cl₂ / 25 h / 20 °C

7.1: 98 percent / Bu₄NF / tetrahydrofuran / 6 h / 0 °C

8.1: BH₃*Me₂S / diethyl ether; tetrahydrofuran / 2.5 h / 20 °C

8.2: 76 percent / H₂O₂; NaOH / diethyl ether; tetrahydrofuran / 2 h / 0 - 20 °C

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