(9AR)-Hexahydropyrazino-[2,1-c][1,4]oxazin-4(3H)-one

Base Information

• Chemical Name: (9AR)-Hexahydropyrazino-[2,1-c][1,4]oxazin-4(3H)-one
• CAS No.: 930783-26-9
• Molecular Formula: C₇H₁₂N₂O₂
• Molecular Weight: 156.184
• DSSTox Substance ID: DTXSID801224439
• Mol file: 930783-26-9.mol

Synonyms:930783-26-9;(9AR)-Hexahydropyrazino-[2,1-c][1,4]oxazin-4(3H)-one;(9aR)-1,6,7,8,9,9a-hexahydropyrazino[2,1-c][1,4]oxazin-4-one;(9ar)-hexahydropyrazino[2,1-c][1,4]oxazin-4(3h)-one;(R)-Hexahydropyrazino[2,1-c][1,4]oxazin-4(3H)-one;SCHEMBL994956;(R)-Hexahydro-pyrazino[2,1-c][1,4]oxazin-4-one;MTCWTJKARNZOLR-ZCFIWIBFSA-N;DTXSID801224439;CS-0055455;P13420;(R)-Hexahydro-pyrazino[2,1-c] [1,4]oxazin-4-one

Chemical Property of (9AR)-Hexahydropyrazino-[2,1-c][1,4]oxazin-4(3H)-one

Chemical Property:

• XLogP3: -1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 156.089877630
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

97% ^*data from raw suppliers

(9AR)-Hexahydropyrazino-[2,1-c][1,4]oxazin-4(3H)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN2C(CN1)COCC2=O
• Isomeric SMILES: C1CN2[C@H](CN1)COCC2=O

Technology Process of (9AR)-Hexahydropyrazino-[2,1-c][1,4]oxazin-4(3H)-one

There total 4 articles about (9AR)-Hexahydropyrazino-[2,1-c][1,4]oxazin-4(3H)-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: 76.0%

(R)-4-oxohexahydropyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester (1147422-40-9) → (R)-hexahydropyrazino[2,1-c][1,4]oxazin-4-one (930783-26-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

(R)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate (278788-66-2) → (R)-hexahydropyrazino[2,1-c][1,4]oxazin-4-one (930783-26-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 5 h / 0 - 20 °C

2: potassium tert-butylate / tetrahydrofuran / 1.25 h / 0 °C

3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With potassium tert-butylate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm3003747

Reference yield:

(R)-4-(2-chloroacetyl)-3-(hydroxymethyl)piperazine-1-carboxylic acid tert-butyl ester (1147422-39-6) → (R)-hexahydropyrazino[2,1-c][1,4]oxazin-4-one (930783-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butylate / tetrahydrofuran / 1.25 h / 0 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With potassium tert-butylate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm3003747

upstream raw materials:

(R)-4-oxohexahydropyrazino[2,1-c][1,4]oxazine-8-carboxylic acid tert-butyl ester

(R)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate

(R)-4-(2-chloroacetyl)-3-(hydroxymethyl)piperazine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(R)-octahydropiperazine[2,1-c][1,4]oxazine