L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide

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Chemical Name:L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide
CAS No.:189218-00-6
Molecular Formula:C₃₅H₄₄FNO₃
Molecular Weight:545.738
Hs Code.:

Synonyms:L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide

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Chemical Property of L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide

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Technology Process of L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide

There total 8 articles about L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide 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: 62.0%

: 232926-00-0
2(R)-(benzyloxymethyl)hexyl iodide

: 189217-97-8
L-prolinol 4-(4-fluorophenyl)phenylbutanamide

: 189218-00-6
L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide

Guidance literature:: L-prolinol 4-(4-fluorophenyl)phenylbutanamide; With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at 20 ℃; for 0.25h;

2(R)-(benzyloxymethyl)hexyl iodide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; cyclohexane; at -82 - -20 ℃;
DOI:10.1016/S0040-4020(99)00334-8

Reference yield:

: 142-61-0
Hexanoyl chloride

: 189218-00-6
L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / n-butyllithium / pentane; tetrahydrofuran / -78 - 0 °C

2.1: titanium(IV) chloride; triethylamine / CH₂Cl₂ / 1 h / 0 °C

2.2: 90 percent / CH₂Cl₂ / 5 h / 0 - 20 °C

3.1: 96 percent / hydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 1 h / 0 °C

4.1: 98 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

5.1: 74 percent / N-iodosuccinimide; triphenylphosphine / dimethylformamide / 2 h / 0 - 20 °C

6.1: LDA / cyclohexane; tetrahydrofuran / 0.25 h / 20 °C

6.2: 62 percent / DMPU / cyclohexane; tetrahydrofuran / -82 - -20 °C

With lithium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; titanium tetrachloride; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; pentane; 1.1: Acylation / 2.1: Metallation / 2.2: Alkylation / 3.1: Hydrolysis / 4.1: Reduction / 5.1: Substitution / 6.1: Metallation / 6.2: Alkylation;
DOI:10.1016/S0040-4020(99)00334-8

Reference yield:

: 143965-32-6
(4S)-3-hexanoyl-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 189218-00-6
L-prolinol 5-benzyloxy-4(S)-n-butyl-2(R)-[2-(4-(4-fluorophenyl)phenyl)ethyl]pentanamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: titanium(IV) chloride; triethylamine / CH₂Cl₂ / 1 h / 0 °C

1.2: 90 percent / CH₂Cl₂ / 5 h / 0 - 20 °C

2.1: 96 percent / hydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 1 h / 0 °C

3.1: 98 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

4.1: 74 percent / N-iodosuccinimide; triphenylphosphine / dimethylformamide / 2 h / 0 - 20 °C

5.1: LDA / cyclohexane; tetrahydrofuran / 0.25 h / 20 °C

5.2: 62 percent / DMPU / cyclohexane; tetrahydrofuran / -82 - -20 °C

With lithium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; dihydrogen peroxide; titanium tetrachloride; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Hydrolysis / 3.1: Reduction / 4.1: Substitution / 5.1: Metallation / 5.2: Alkylation;
DOI:10.1016/S0040-4020(99)00334-8