(R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester

Base Information

Chemical Name:(R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester
CAS No.:505086-79-3
Molecular Formula:C₂₈H₃₀N₂O₇
Molecular Weight:506.555
Hs Code.:

Synonyms:(R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Property of (R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of (R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester

There total 2 articles about (R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl 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: 68.0%

: 120-72-9
indole

: 2033-24-1
cycl-isopropylidene malonate

: 117833-92-8
(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

: 505086-79-3
(R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: With rac-Pro-OH; In acetonitrile;
DOI:10.1016/S0040-4039(02)02537-6

Reference yield:

: 117833-99-5
N-benzyloxycarbonyl 4(S)-(1'-methoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

: 505086-79-3
(R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: DIBAL / toluene / 0.5 h / -78 °C

2: 1.04 g / DL-proline / acetonitrile / 15 h / 20 °C

With diisobutylaluminium hydride; rac-Pro-OH; In toluene; acetonitrile;
DOI:10.1016/j.tetasy.2005.02.008

Reference yield:

: 505086-79-3
(R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester

: 505086-85-1
(3S,4R,5R)-[5-(tertbutyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxopyrrolidin-3-yl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: AcOH; H₂ / Pd/C / ethanol / 20 h / 20 °C

1.2: 63 percent / methanol; diethyl ether / 0.5 h / 0 °C

2.1: 80 percent / imidazole / dimethylformamide

3.1: 87 percent / aq. KOH / tetrahydrofuran / 20 °C

4.1: DPPA; Et₃N / acetonitrile / 2.5 h / 0 - 20 °C

4.2: tetrahydrofuran / 1 h / Heating

4.3: 80 percent / tetrahydrofuran / 24 h / Heating

With 1H-imidazole; potassium hydroxide; diphenyl-phosphinic acid; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile; 4.2: Curtius rearrangement;
DOI:10.1016/j.tetasy.2005.02.008