(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile

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Chemical Name:(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile
CAS No.:895579-25-6
Molecular Formula:C₂₀H₂₈N₂O₃Si
Molecular Weight:372.539
Hs Code.:

Synonyms:(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile

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Chemical Property of (2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile

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Technology Process of (2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile

There total 10 articles about (2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile 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:

: 895579-24-5
(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-cyano-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester

: 895579-25-6
(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 6h;
DOI:10.1021/ja061970a

Reference yield:

: 895579-14-3
(E)-3-(allyldimethylsilyl)acrylaldehyde

: 895579-25-6
(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; sodium chlorite / 2-methyl-propan-2-ol / 0.5 h / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

2.2: 15.3 g / 1,1-carbonyldiimidazole / tetrahydrofuran; hexane / 0.83 h / -5 °C

3.1: (S,S)-[(salen)Al]O / cyclohexane; 2-methyl-propan-2-ol / 120 h / 23 °C

4.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: tetrahydrofuran / 4 h / -78 - 0 °C

5.1: sodium borohydride / methanol / 6 h / 0 °C

With sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; lithium hexamethyldisilazane; [((S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine(-2H))Al]2O; In tetrahydrofuran; methanol; hexane; cyclohexane; tert-butyl alcohol;
DOI:10.1021/ja061970a

Reference yield:

: 895579-11-0
3-(allyldimethylsilyl)prop-2-yn-1-ol

: 895579-25-6
(2R,3R,4S)-3-(Allyl-dimethyl-silanyl)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carbonitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: Red-Al(R) / diethyl ether; toluene / 1 h / 0 - 20 °C

2.1: dimethylsulfoxide; triethylamine; SO₃*pyridine / CH₂Cl₂ / 5.5 h / 0 - 20 °C

3.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; sodium chlorite / 2-methyl-propan-2-ol / 0.5 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

4.2: 15.3 g / 1,1-carbonyldiimidazole / tetrahydrofuran; hexane / 0.83 h / -5 °C

5.1: (S,S)-[(salen)Al]O / cyclohexane; 2-methyl-propan-2-ol / 120 h / 23 °C

6.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.2: tetrahydrofuran / 4 h / -78 - 0 °C

7.1: sodium borohydride / methanol / 6 h / 0 °C

With sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; [((S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine(-2H))Al]2O; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; tert-butyl alcohol;
DOI:10.1021/ja061970a