(S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one

Base Information

• Chemical Name: (S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one
• CAS No.: 203871-49-2
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.181
• Mol file: 203871-49-2.mol

Synonyms:(S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one

Chemical Property of (S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one

There total 1 articles about (S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]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:

(S)-Pyroglutaminol (17342-08-4) → (S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one (203871-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CSA

2: 1.) PhSeH

With camphor-10-sulfonic acid; Benzeneselenol;

DOI:10.1016/S0040-4039(97)10807-3

Reference yield: 59.0%

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) + (S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one (203871-49-2) → (5aS,8aR,8bS)-7-benzyl-3,3-dimethylhexahydro-1H-pyrrolo[3',4':3,4]pyrrolo[1,2-c]oxazol-5(3H)-one

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 40 ℃; for 36h; Inert atmosphere;

Reference yield:

(S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one (203871-49-2) → 1-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-4-[2-(1r,4r)-(4-formylcyclohexyl)ethynyl]-7-methoxyisoquinoline-6-carboxamide

Guidance literature:

Multi-step reaction with 8 steps

1.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 1 h / -65 - -45 °C / Inert atmosphere

1.2: 1 h / -72 - -65 °C / Inert atmosphere

1.3: 4.5 h / -72 - -60 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: trifluoroacetic acid / water; acetonitrile / 4 h / 65 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / N,N-dimethyl-formamide; tetrahydrofuran / 0.75 h / -10 °C / Inert atmosphere

5.1: N-Bromosuccinimide / acetonitrile / 2 h / 60 °C / Inert atmosphere

6.1: potassium carbonate / water; dimethyl sulfoxide / 16 h / 25 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

8.1: Dess-Martin periodane / dichloromethane / 3 h / 25 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; copper(l) iodide; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

(S)-Pyroglutaminol

Downstream raw materials:

(3S,4S,5S)-4-ethyl-3-fluoro-5-(hydroxymethyl)-pyrrolidin-2-one

(1S,4S,5R)-4-(hydroxymethyl)-3-azabicyclo[3.1.0]hexan-2-one

PF-06650833