(3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:910137-77-8
Molecular Formula:C₁₉H₂₅NO₇
Molecular Weight:379.41
Hs Code.:

Synonyms:(3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 12 articles about (3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 86.0%

: 910137-76-7
(3R,4R)-4-Benzoyloxy-3,8,8-trimethyl-2-oxo-7,9-dioxa-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

: 910137-77-8
(3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃;
DOI:10.1016/j.tetlet.2006.06.117

Reference yield:

: 910137-71-2
(R)-4-((1R,2S)-1,3-Dihydroxy-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 910137-77-8
(3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 82 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 91 percent / NaH / dimethylformamide / 0 °C

3: 89 percent / TBAF / tetrahydrofuran / 20 °C

4: 97 percent / Et₃N / CH₂Cl₂ / 20 °C

5: 63 percent / p-TSA / methanol / 20 °C

6: IBX; DMSO / tetrahydrofuran / 20 °C

7: NaOH / tetrahydrofuran; H₂O / 20 °C

8: 85 percent / p-TSA / 20 °C

9: 82 percent / RyCl₃; aq. NaIO₄ / ethyl acetate / 20 °C

10: 86 percent / p-TSA / methanol / 20 °C

With dmap; sodium hydroxide; sodium periodate; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2006.06.117

Reference yield:

: 1025808-77-8
(2S,3R,4S)-3-Benzyloxy-2-formyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 910137-77-8
(3R,4R)-3-Benzoyloxy-2,2-bis-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaOH / tetrahydrofuran; H₂O / 20 °C

2: 85 percent / p-TSA / 20 °C

3: 82 percent / RyCl₃; aq. NaIO₄ / ethyl acetate / 20 °C

4: 86 percent / p-TSA / methanol / 20 °C

With sodium hydroxide; sodium periodate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; ethyl acetate;
DOI:10.1016/j.tetlet.2006.06.117