(2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine

Base Information

• Chemical Name: (2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine
• CAS No.: 108082-56-0
• Molecular Formula: C₁₇H₂₇NO₅
• Molecular Weight: 325.405

Synonyms:(2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine

Chemical Property of (2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine

There total 12 articles about (2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2S,3S,4S,5R)-3,4-Bis-methoxymethoxy-2-(4-methoxy-phenyl)-5-methyl-pyrrolidine (99891-38-0,108082-48-0,108082-53-7) → (2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine (108082-56-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; for 0.5h; under 760 Torr;

DOI:10.1021/jo00386a012

Reference yield:

4-O-benzyl-2,3-O-bis(methoxymethyl)-L-threose (99878-63-4) → (2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine (108082-56-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Mg / 1.) THF, reflux, 2.) THF, RT, 10 h

2: 32 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 12 h / Ambient temperature

3: 71 percent / H₂ / 10percent Pd on C / methanol / 1 h / 760 Torr

4: 1.) oxalyl chloride, Me₂SO / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) RT, 1 h

5: 1.) Mg / 1.) Et₂O, 2.) Et₂O, -78 deg C, 2 h

6: hydrazine hydrate / ethanol / 2.5 h / Heating

7: Na₂CO₃ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

8: triethylamine / CH₂Cl₂ / 0.17 h / 0 - 20 °C

9: H₂ / 10percent Pd on C / methanol / 1 h / 760 Torr

10: H₂ / 10percent Pd on C / H₂O / 0.5 h / 760 Torr

With oxalyl dichloride; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1021/jo00386a012

Reference yield:

(1R,2S,3S)-4-(benzyloxy)-2,3-bis<(methoxymethyl)oxy>-1-(p-methoxyphenyl)-1-butanol (99878-64-5) → (2S,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine (108082-56-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 32 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 12 h / Ambient temperature

2: 71 percent / H₂ / 10percent Pd on C / methanol / 1 h / 760 Torr

3: 1.) oxalyl chloride, Me₂SO / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) RT, 1 h

4: 1.) Mg / 1.) Et₂O, 2.) Et₂O, -78 deg C, 2 h

5: hydrazine hydrate / ethanol / 2.5 h / Heating

6: Na₂CO₃ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

7: triethylamine / CH₂Cl₂ / 0.17 h / 0 - 20 °C

8: H₂ / 10percent Pd on C / methanol / 1 h / 760 Torr

9: H₂ / 10percent Pd on C / H₂O / 0.5 h / 760 Torr

With oxalyl dichloride; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1021/jo00386a012

upstream raw materials:

formaldehyd

(2S,3S,4S,5R)-3,4-Bis-methoxymethoxy-2-(4-methoxy-phenyl)-5-methyl-pyrrolidine

4-O-benzyl-2,3-O-bis(methoxymethyl)-L-threose

(1R,2S,3S)-4-(benzyloxy)-2,3-bis<(methoxymethyl)oxy>-1-(p-methoxyphenyl)-1-butanol

Downstream raw materials:

(2S,3S,4S,5R)-3,4-dihydroxy-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine (codonopsinine stereoisomer 1d)

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