(2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

Base Information

Chemical Name:(2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine
CAS No.:138528-06-0
Molecular Formula:C₁₈H₂₇NO₄
Molecular Weight:321.417
Hs Code.:

Synonyms:(2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

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Chemical Property of (2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

Chemical Property:

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Technology Process of (2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

There total 30 articles about (2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-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:

: 24424-99-5
di-tert-butyl dicarbonate

: 138528-06-0
(2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

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

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

4: 66 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

5: 63 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

6: 1.) potassium carbonate; 2.) sodium borohydride / 1.) methanol, reflux, 2 h; 2.) methanol, room temp., 30 min

With dmap; sodium tetrahydroborate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; triethylamine; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

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

: 138528-06-0
(2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 8 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: 66 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

7: 63 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

8: 1.) potassium carbonate; 2.) sodium borohydride / 1.) methanol, reflux, 2 h; 2.) methanol, room temp., 30 min

With dmap; sodium tetrahydroborate; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; 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

: 138528-06-0
(2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 6 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: 66 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

5: 63 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

6: 1.) potassium carbonate; 2.) sodium borohydride / 1.) methanol, reflux, 2 h; 2.) methanol, room temp., 30 min

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