(2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine

Base Information

Chemical Name:(2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine
CAS No.:159411-96-8
Molecular Formula:C₂₀H₂₅NO₂
Molecular Weight:311.424
Hs Code.:

Synonyms:

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Chemical Property of (2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine

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Technology Process of (2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine

There total 20 articles about (2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine 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:

: 56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
L-glutamic acid

: 159411-96-8
(2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 12 steps

1: 43 percent / 2M sodium hydroxide, sodium borohydride / H₂O / 3.5 h / Ambient temperature

2: 88 percent / thionyl chloride / 3 h / Heating

3: 95 percent / lithium chloride, sodium borohydride / ethanol; tetrahydrofuran / 2 h / Ambient temperature

4: 96 percent / NaH / dimethylformamide; paraffin / 1 h / Ambient temperature

5: 83 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 2 h / Ambient temperature

6: 98 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

7: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 °C

8: pyridinium p-toluenesulfonate / 3 h / Ambient temperature

9: 29 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

10: 66 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

11: sodium borohydride / methanol / 0.17 h / Ambient temperature

12: sodium hydrogen carbonate / CH₂Cl₂; H₂O / 20 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; lithium chloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; triethylamine; N,N-dimethyl-formamide; toluene; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

: 152500-26-0
(S)-5-(hydroxymethyl)-1-(4-methoxyphenylmethyl)-2-pyrrolidinone

: 159411-96-8
(2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / NaH / dimethylformamide; paraffin / 1 h / Ambient temperature

2: 83 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 2 h / Ambient temperature

3: 98 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

4: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 °C

5: pyridinium p-toluenesulfonate / 3 h / Ambient temperature

6: 29 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

7: 66 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

8: sodium borohydride / methanol / 0.17 h / Ambient temperature

9: sodium hydrogen carbonate / CH₂Cl₂; H₂O / 20 h / Ambient temperature

With dmap; sodium tetrahydroborate; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; triethylamine; N,N-dimethyl-formamide; toluene; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

: 108963-96-8
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

: 159411-96-8
(2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: diisobutylaluminium hydride / hexane; tetrahydrofuran / -78 deg C, 1 h, then 0 deg C, 2 h

2: pyridinium p-toluenesulfonate / 12 h / Ambient temperature

3: NaH / paraffin; dimethylformamide / 1 h / Ambient temperature

4: 29 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

5: 66 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

6: sodium borohydride / methanol / 0.17 h / Ambient temperature

7: sodium hydrogen carbonate / CH₂Cl₂; H₂O / 20 h / Ambient temperature

With sodium tetrahydroborate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; paraffin;
DOI:10.1016/S0040-4020(01)80643-8