(2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline

Base Information

Chemical Name:(2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline
CAS No.:118014-68-9
Molecular Formula:C₂₁H₂₉NO₃
Molecular Weight:343.466
Hs Code.:

Synonyms:(2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline

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Technology Process of (2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline

There total 16 articles about (2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline 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: 79.0%

: 118014-67-8
(2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-pentenyl)-3-pyrroline

: 118014-68-9
(2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline

Guidance literature:: With oxygen; copper dichloride; palladium dichloride; In water; N,N-dimethyl-formamide; at 70 ℃; for 0.666667h;
DOI:10.1021/ja00186a038

Reference yield:

: 117941-01-2
(2S,3S,4S)-1-(Benzyloxy)-2,3-bis<(methoxymethyl)oxy>octan-4-ol

: 118014-68-9
(2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline

Guidance literature:: Multi-step reaction with 13 steps

1: 61 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

2: 71 percent / H₂ / 10percent Pd/C / methanol / 3 h

3: 94 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

4: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min

5: 85 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

6: 68 percent / 0.14 M Zn(BH₄)2 / diethyl ether / 0.75 h / 0 °C

7: hydrazine hydrate / ethanol / 2 h / Heating

8: aq. Na₂CO₃ / CH₂Cl₂ / 0.08 h / 0 °C

9: triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

10: t-BuOK / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) room temp., 10 min

11: 95 percent / concentrated HCl / methanol / 0.5 h / Heating

12: 79 percent / triphenylphosphine, imidazole, 2,4,5-triiodoimidazole, zinc dust / toluene / 4 h / Heating

13: 79 percent / O₂, PdCl₂, CuCl₂ / dimethylformamide; H₂O / 0.67 h / 70 °C

With 1H-imidazole; hydrogenchloride; 2,4,5-triiodoimidazole; zinc(II) tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen; oxygen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; copper dichloride; palladium dichloride; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00186a038

Reference yield:

: 117941-07-8
(2S,3S,4R)-1-(Benzyloxy)-4-(1,3-dioxo-2-azaindan-2-yl)-2,3-bis<(methoxymethyl)oxy>octane

: 118014-68-9
(2R,5R)-N-<(Benzyloxy)carbonyl>-5-butyl-2-(4-oxopentyl)-3-pyrroline

Guidance literature:: Multi-step reaction with 12 steps

1: 71 percent / H₂ / 10percent Pd/C / methanol / 3 h

2: 94 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

3: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min

4: 85 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

5: 68 percent / 0.14 M Zn(BH₄)2 / diethyl ether / 0.75 h / 0 °C

6: hydrazine hydrate / ethanol / 2 h / Heating

7: aq. Na₂CO₃ / CH₂Cl₂ / 0.08 h / 0 °C

8: triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

9: t-BuOK / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) room temp., 10 min

10: 95 percent / concentrated HCl / methanol / 0.5 h / Heating

11: 79 percent / triphenylphosphine, imidazole, 2,4,5-triiodoimidazole, zinc dust / toluene / 4 h / Heating

12: 79 percent / O₂, PdCl₂, CuCl₂ / dimethylformamide; H₂O / 0.67 h / 70 °C

With 1H-imidazole; hydrogenchloride; 2,4,5-triiodoimidazole; zinc(II) tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen; oxygen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; copper dichloride; palladium dichloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00186a038