(3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

Base Information

Chemical Name:(3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one
CAS No.:137683-86-4
Molecular Formula:C₉H₁₅NO₄
Molecular Weight:201.222
Hs Code.:

Synonyms:(3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

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Chemical Property of (3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

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Technology Process of (3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

There total 2 articles about (3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-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: 61.0%

: 137664-63-2
(3aR,6R,6aR)-5-(4-Methoxy-benzyl)-6-methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

: 137664-66-5
(3aR,6R,6aR)-5-(4-Methoxy-benzoyl)-6-methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

: 137683-86-4
(3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

Guidance literature:: With ammonium cerium(IV) nitrate; In acetonitrile;
DOI:10.1021/ja992135e

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 137683-86-4
(3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

Guidance literature:: Multi-step reaction with 11 steps

1: 72 percent / TsOH

2: LDA

3: aq. H₂O₂

4: OsO₄; NMO

5: TsOH / acetone

6: 73 percent / NH₂NH₂; 10 percent Pd/C / methanol / Heating

7: NaH / tetrahydrofuran; dimethylformamide

8: H₂ / Pd(OH)2 / ethanol / 2585.74 Torr

9: 97 percent / NaH / tetrahydrofuran; dimethylformamide

10: 24 percent / aq. cerium(IV) ammonium nitrate / acetonitrile

11: 80 percent / aq. LiOOH / tetrahydrofuran

With palladium on activated charcoal; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; lithium hydroperoxide; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; hydrazine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Cyclization / 2: Metallation / 2: selenylation / 3: oxidative olefination / 4: Oxidation / 5: transacetalization / 6: Ring cleavage / 7: protection / 8: Hydrogenolysis / 9: Methylation / 10: deprotection / 11: Hydrolysis;
DOI:10.1021/ja992135e

Reference yield:

: 137683-86-4
(3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

: ((R)-1-{(4R,5R)-5-[(R)-3-(4-Benzyloxymethyl-oxazol-2-yl)-butylcarbamoyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxy-ethyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / DMAP / tetrahydrofuran / Heating

2: 70 percent / AlMe₃ / benzene

With dmap; trimethylaluminum; In tetrahydrofuran; benzene; 1: Acylation / 2: Condensation;
DOI:10.1021/ja992135e