(3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Base Information

• Chemical Name: (3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
• CAS No.: 247589-86-2
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.428

Synonyms:(3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Chemical Property of (3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Chemical Property:

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Technology Process of (3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

There total 2 articles about (3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-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: 96.0%

benzyl chloride (100-44-7) + (3S,6S,7aR)-6-Hydroxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (247589-85-1) → (3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (247589-86-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 25 ℃;

DOI:10.1039/a903160j

Reference yield:

(3S,7aR)-3-isopropyl-7a-methyltetrahydropyrrolo[2,1-b][1,3]-oxazol-5-one (98203-44-2) → (3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (247589-86-2)

Guidance literature:

Multi-step reaction with 2 steps

2: 96 percent / NaH / dimethylformamide / 0 - 25 °C

With sodium hydride; In N,N-dimethyl-formamide; 2: Etherification;

DOI:10.1039/a903160j

Reference yield:

(3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (247589-86-2) → (3S,6S,7aR)-6-Benzyloxymethyl-3-isopropyl-6,7a-dimethyl-hexahydro-pyrrolo[2,1-b]oxazol-5-ol

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; at -25 ℃; for 48h;

DOI:10.1039/a903160j

upstream raw materials:

benzyl chloride

(3S,6S,7aR)-6-Hydroxymethyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

(3S,7aR)-3-isopropyl-7a-methyltetrahydropyrrolo[2,1-b][1,3]-oxazol-5-one

Downstream raw materials:

(R)-4-Benzyloxymethyl-4-methyl-cyclopent-2-enone

(1S,4R)-4-Benzyloxymethyl-4-methyl-cyclopent-2-enol

(1R,4R)-4-Benzyloxymethyl-4-methyl-cyclopent-2-enol

1-((1S,4R)-4-Benzyloxymethyl-4-methyl-cyclopent-2-enyloxymethyl)-4-methoxy-benzene

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