{2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester

Base Information

• Chemical Name: {2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester
• CAS No.: 301838-62-0
• Molecular Formula: C₂₀H₂₆N₂O₆
• Molecular Weight: 390.436

Synonyms:{2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester

Chemical Property of {2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester

Chemical Property:

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Technology Process of {2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester

There total 13 articles about {2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester 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: 77.0%

{2-[(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-eth-(E)-ylidene-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester (301838-55-1) → {2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester (301838-62-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0960-894X(00)00351-6

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → {2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester (301838-62-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / LiBH₄ / tetrahydrofuran / 0 °C

2: 70 percent / TEA; DBU / CH₂Cl₂

3: 100 percent / H₂ / 10 percent Pd-C / ethanol

4: TEA / CH₂Cl₂ / 0 °C

5: 95 percent / Raney Ni; NH₂NH₂ / methanol / Heating

6: 87 percent / pyridine / CH₂Cl₂ / 0 °C

7: 98 percent / (COCl)2; DMSO; TEA / CH₂Cl₂ / -60 °C

8: 64 percent / t-BuOK / tetrahydrofuran

9: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

With pyridine; lithium borohydride; oxalyl dichloride; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; nickel; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Reduction / 2: silylation / 3: Hydrogenolysis / 4: Acylation / 5: Reduction / 6: Acylation / 7: Swern oxidation / 8: Wittig olefination / 9: desilylation;

DOI:10.1016/S0960-894X(00)00351-6

Reference yield:

(2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(hydroxymethyl)-pyrrolidine (95687-41-5,1448706-36-2) → {2-[(S)-4-Eth-(E)-ylidene-2-hydroxymethyl-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester (301838-62-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 70 percent / TEA; DBU / CH₂Cl₂

2: 100 percent / H₂ / 10 percent Pd-C / ethanol

3: TEA / CH₂Cl₂ / 0 °C

4: 95 percent / Raney Ni; NH₂NH₂ / methanol / Heating

5: 87 percent / pyridine / CH₂Cl₂ / 0 °C

6: 98 percent / (COCl)2; DMSO; TEA / CH₂Cl₂ / -60 °C

7: 64 percent / t-BuOK / tetrahydrofuran

8: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

With pyridine; oxalyl dichloride; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; nickel; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: silylation / 2: Hydrogenolysis / 3: Acylation / 4: Reduction / 5: Acylation / 6: Swern oxidation / 7: Wittig olefination / 8: desilylation;

DOI:10.1016/S0960-894X(00)00351-6

upstream raw materials:

{2-[(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-eth-(E)-ylidene-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenyl}-carbamic acid allyl ester

4,5-dimethoxy-2-nitro-benzoic acid

4,5-dimethoxy-2-nitrobenzoyl chloride

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

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