(4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one

Base Information

Chemical Name:(4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one
CAS No.:366479-76-7
Molecular Formula:C₃₂H₃₉NO₅SSi
Molecular Weight:577.817
Hs Code.:

Synonyms:(4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one

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Chemical Property of (4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one

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Technology Process of (4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one

There total 1 articles about (4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one 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: 69.0%

: 366479-75-6
(4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one

: 74-88-4
methyl iodide

: 366479-76-7
(4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one

Guidance literature:: (4S,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-4-vinylpyrrolidin-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -10 ℃; for 0.166667h;

methyl iodide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at -10 - 20 ℃; for 2.5h; Further stages.;
DOI:10.1021/jm010096n

Reference yield: 56.0%

: 366479-76-7
(4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one

: 366479-77-8
(2R,3R)-[1-(4-methoxybenzenesulfonyl)-4,4-dimethyl-3-vinylpyrrolidin-2-yl]methanol

Guidance literature:: (4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one; With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; Further stages.;
DOI:10.1021/jm010096n

Reference yield:

: 366479-76-7
(4R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-methoxybenzenesulfonyl)-3,3-dimethyl-4-vinylpyrrolidin-2-one

: (2R,3R)-1-(4-Methoxy-benzenesulfonyl)-4,4-dimethyl-3-phenethylsulfanylmethyl-pyrrolidine-2-carboxylic acid hydroxyamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

1.2: 56 percent / BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / 0 - 20 °C

2.1: NaClO₂; NaOCl; TEMPO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.5

3.1: 0.736 g / diethyl ether / 0.08 h / 20 °C

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: Me₂S / CH₂Cl₂ / 0.5 h / -78 - 20 °C

4.3: 69 percent / NaBH₄ / CH₂Cl₂; ethanol / 2 h / 20 °C

5.1: Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

6.1: NaH / dimethylformamide / 0.08 h / 20 °C

6.2: 49 percent / dimethylformamide / 20 °C

7.1: 79 percent / NH₂OK; NH₂OH / methanol / 72 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; lithium aluminium tetrahydride; hydroxylamine potassium salt; hydroxylamine; sodium hydride; ozone; triethylamine; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm010096n