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

Base Information

Chemical Name:(2R,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine
CAS No.:108082-54-8
Molecular Formula:C₁₇H₂₇NO₅
Molecular Weight:325.405
Hs Code.:

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

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

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

There total 13 articles about (2R,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: 84.0%

: 108082-52-6
(2R,3S,4S,5R)-N-<(benzyloxy)carbonyl>-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-5-methylpyrrolidine

: 108082-54-8
(2R,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;
DOI:10.1021/jo00386a012

Reference yield:

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 108082-53-7
(2R,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-5-methylpyrrolidine

: 108082-54-8
(2R,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine

Guidance literature:: With hydrogen; palladium on activated charcoal; In water; for 0.5h; under 760 Torr;
DOI:10.1021/jo00386a012

Reference yield:

: 99878-64-5
(1R,2S,3S)-4-(benzyloxy)-2,3-bis<(methoxymethyl)oxy>-1-(p-methoxyphenyl)-1-butanol

: 108082-54-8
(2R,3S,4S,5R)-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine

Guidance literature:: Multi-step reaction with 11 steps

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

2: 75 percent / H₂ / 10percent Pd on C / methanol / 3.5 h / 760 Torr

3: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 - 20 deg C

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

5: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 - 20 deg C

6: 60 percent / NaBH₄ / ethanol / 1 h / 0 °C

7: hydrazine hydrate / ethanol / 2.5 h / Heating

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

9: 86 percent / triethylamine / CH₂Cl₂ / 0.17 h / 0 - 20 °C

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

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

With sodium tetrahydroborate; 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