(2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine

Base Information

Chemical Name:(2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine
CAS No.:442887-25-4
Molecular Formula:C₁₉H₃₀N₂O₅
Molecular Weight:366.458
Hs Code.:

Synonyms:(2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine

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Chemical Property of (2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine

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Technology Process of (2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine

There total 14 articles about (2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine 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: 100.0%

: 442887-33-4
(2R,4R)-4-acetoxy-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonylpyrrolidine

: 442887-25-4
(2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine

Guidance literature:: With sodium hydroxide; In methanol; at 20 ℃; for 0.5h;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: 442681-67-6
(2R,4R)-1-tert-butoxycarbonyl-2-[(E)-2-(ethoxycarbonyl)vinyl]-4-hydroxypyrrolidine

: 442887-25-4
(2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 12 steps

1.1: PPh₃; diisopropyl azodicarboxylate; AcOH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 82.2 percent / aq. NaOH / ethanol / 0.17 h / 20 °C

2.1: 78.9 percent / imidazole / dimethylformamide / 3 h / 20 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: TBAB / tetrahydrofuran / 24 h / 50 °C

4.1: 27.94 percent / NaCl / dimethylsulfoxide; H₂O / 3 h / 160 °C

5.1: 9.09 g / LiAlH₄ / pyridine / 0.5 h / -20 °C

6.1: 74.9 percent / Me₃P / tetrahydrofuran / 13 h / 50 °C

7.1: 97.5 percent / HgCl₂; Mg / tetrahydrofuran; methanol / 1 h / 18 °C

8.1: H₂ / Raney Ni / methanol / 22 h / 20 °C / 2660 Torr

9.1: 5.74 g / iPr₂NEt / tetrahydrofuran; H₂O / 0 °C

10.1: 10 percent HCl / methanol / 20 h / 20 °C

10.2: 80.7 percent / aq. NaOH / dioxane; H₂O / 20 °C / pH 8.5

11.1: 93.7 percent / PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

12.1: 100 percent / aq. NaOH / methanol / 0.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; hydrogen; sodium hydride; magnesium; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium chloride; mercury dichloride; trimethylphosphane; nickel; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.2: Michael addition / 11.1: Mitsunobu reaction;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: 442681-68-7
(2R,4S)-1-tert-butoxycarbonyl-2-[(E)-2-(ethoxycarbonyl)vinyl]-4-hydroxypyrrolidine

: 442887-25-4
(2S,4R)-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonyl-4-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 11 steps

1.1: 78.9 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: TBAB / tetrahydrofuran / 24 h / 50 °C

3.1: 27.94 percent / NaCl / dimethylsulfoxide; H₂O / 3 h / 160 °C

4.1: 9.09 g / LiAlH₄ / pyridine / 0.5 h / -20 °C

5.1: 74.9 percent / Me₃P / tetrahydrofuran / 13 h / 50 °C

6.1: 97.5 percent / HgCl₂; Mg / tetrahydrofuran; methanol / 1 h / 18 °C

7.1: H₂ / Raney Ni / methanol / 22 h / 20 °C / 2660 Torr

8.1: 5.74 g / iPr₂NEt / tetrahydrofuran; H₂O / 0 °C

9.1: 10 percent HCl / methanol / 20 h / 20 °C

9.2: 80.7 percent / aq. NaOH / dioxane; H₂O / 20 °C / pH 8.5

10.1: 93.7 percent / PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

11.1: 100 percent / aq. NaOH / methanol / 0.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; hydrogen; sodium hydride; magnesium; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium chloride; mercury dichloride; trimethylphosphane; nickel; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.2: Michael addition / 10.1: Mitsunobu reaction;
DOI:10.1016/S0968-0896(01)00430-8