(4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:215171-13-4
Molecular Formula:C₁₇H₂₅NO₄
Molecular Weight:307.39
Hs Code.:

Synonyms:(4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 6 articles about (4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-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%

: 215171-12-3
(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 215171-13-4
(4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Heating;
DOI:10.1016/S0040-4020(98)00741-8

Reference yield:

: 100-58-3
phenylmagnesium bromide

: 215171-13-4
(4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) Et₂AlCl / 1.) Et₂O, room temp., 15 min, 2.) Et₂O, -60 deg C, 6 h

2: 1.) H₂ / 1.) Pd(OH)2/C / 1.) MeOH, 70 psi, 3 d, 2.) 1,4-dioxane, room temp., 16 h

3: 96 percent / p-toluensulfonic acid monohydrate / methanol / 4 h / Heating

4: 91 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

5: 80 percent / (1R)-(-)-10-camphorsulfonic acid / acetone / 0.5 h / Ambient temperature

6: 86 percent / Bu₄NF / tetrahydrofuran / 1 h / Heating

With 1H-imidazole; dmap; (R)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diethylaluminium chloride; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(98)00741-8

Reference yield:

: 192764-06-0
N-Benzyl-N-[(R)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-hydroxylamine

: 215171-13-4
(4R,5S)-5-Hydroxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) H₂ / 1.) Pd(OH)2/C / 1.) MeOH, 70 psi, 3 d, 2.) 1,4-dioxane, room temp., 16 h

2: 96 percent / p-toluensulfonic acid monohydrate / methanol / 4 h / Heating

3: 91 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

4: 80 percent / (1R)-(-)-10-camphorsulfonic acid / acetone / 0.5 h / Ambient temperature

5: 86 percent / Bu₄NF / tetrahydrofuran / 1 h / Heating

With 1H-imidazole; dmap; (R)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(98)00741-8