(2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde

Base Information

Chemical Name:(2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde
CAS No.:445469-17-0
Molecular Formula:C₁₉H₂₉NO₃Si
Molecular Weight:347.53
Hs Code.:

Synonyms:(2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde

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Chemical Property of (2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde

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Technology Process of (2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde

There total 4 articles about (2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde 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: 97.0%

: 445469-16-9
(1'S,2'R,5R)-1-benzyl-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]pyrrolidin-2-one

: 445469-17-0
(2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde

Guidance literature:: With sodium periodate; silica gel; In dichloromethane; water; at 20 ℃; for 0.5h;
DOI:10.1021/jo0257905

Reference yield:

: 141293-15-4
(1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester

: 445469-17-0
(2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / H₂; NaOAc / Pd/C / ethyl acetate / 24 h / 20 °C

2.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 20 °C

3.1: 93 percent / ammonium cerium(IV) nitrate / acetonitrile / 4 h / 80 °C

4.1: NaH / tetrahydrofuran / 0.17 h / 20 °C

4.2: 91 percent / tetrahydrofuran / 1.5 h / Heating

5.1: 98 percent / H₂IO₆ / ethyl acetate / 1 h / 20 °C

With 2,6-dimethylpyridine; ammonium cerium(IV) nitrate; hydrogen; sodium acetate; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jm050698x

Reference yield:

: 872174-12-4
(1'S,4''R,5R)-5-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]pyrrolidin-2-one

: 445469-17-0
(2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0.17 h / 20 °C

1.2: 91 percent / tetrahydrofuran / 1.5 h / Heating

2.1: 98 percent / H₂IO₆ / ethyl acetate / 1 h / 20 °C

With sodium hydride; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/jm050698x