3,6-Diazabicyclo[3.2.0]heptane-3,6-dicarboxylic acid, 6-(1,1-dimethylethyl) 3-(phenylmethyl) ester, (1R,5S)-

Base Information

• Chemical Name: 3,6-Diazabicyclo[3.2.0]heptane-3,6-dicarboxylic acid, 6-(1,1-dimethylethyl) 3-(phenylmethyl) ester, (1R,5S)-
• CAS No.: 799279-84-8
• Molecular Formula: C18H24N2O4
• Molecular Weight: 332.4
• Mol file: 799279-84-8.mol

Synonyms:3-benzyl,6-tert-butyl-(1R,5S)-3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate;3-benzyl (cis)-6-tert-butyl 3,6-diazabicyclo [3.2.0]heptane-3,6-dicarboxylate;3-benzyl-6-tert-butyl-(1R,5S)-3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate;6-Boc-3-carboxybenzyl-(1R,5S)-3,6-diazabicyclo[3.2.0]heptane;3-benzyl 6-tert-butyl-(1R,5S)-3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate;6-boc-3-caroxybenzyl-(1R,5S)-3,6-diazabicyclo[3.2.0.]heptane;

Chemical Property of 3,6-Diazabicyclo[3.2.0]heptane-3,6-dicarboxylic acid, 6-(1,1-dimethylethyl) 3-(phenylmethyl) ester, (1R,5S)-

Chemical Property:

• Boiling Point: 446.5±28.0 °C(Predicted)
• PSA: 59.08000
• Density: 1.218±0.06 g/cm3(Predicted)
• LogP: 2.75010

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,6-Diazabicyclo[3.2.0]heptane-3,6-dicarboxylic acid, 6-(1,1-dimethylethyl) 3-(phenylmethyl) ester, (1R,5S)-

There total 10 articles about 3,6-Diazabicyclo[3.2.0]heptane-3,6-dicarboxylic acid, 6-(1,1-dimethylethyl) 3-(phenylmethyl) ester, (1R,5S)- 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: 95.4%

benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylate (370881-43-9) + di-tert-butyl dicarbonate (24424-99-5) → (1R,5S)-3-benzyl 6-tert-butyl 3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate (799279-84-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 10h;

DOI:10.1021/jm070755h

Reference yield:

benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate 4-methylbenzenesulfonate + di-tert-butyl dicarbonate (24424-99-5) → (1R,5S)-3-benzyl 6-tert-butyl 3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate (799279-84-8)

Guidance literature:

benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate 4-methylbenzenesulfonate; di-tert-butyl dicarbonate; With potassium carbonate; In water; toluene; at 15 - 30 ℃; for 0.166667h;

With N,N`-dimethylethylenediamine; In water; toluene;

Reference yield:

benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate (252770-09-5,255823-06-4) → (1R,5S)-3-benzyl 6-tert-butyl 3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate (799279-84-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetone / 20 °C

1.2: 48 h / 20 °C

2.1: sulfuric acid / ethanol; water / 16 h / 20 °C

2.2: 4 h / 10 - 20 °C / pH 10

3.1: triethylamine / dichloromethane / 1.5 h / -10 - 20 °C

4.1: dichloromethane / 1 h / 20 °C

5.1: sodium hydroxide / ethanol; water / 1.5 h / 60 °C / pH 12

6.1: ethanol / 0.5 - 1 h / 20 °C

With sodium hydroxide; sulfuric acid; triethylamine; In ethanol; dichloromethane; water; acetone;

upstream raw materials:

benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylate

di-tert-butyl dicarbonate

benzyl (3S,4S)-3-tert-butoxycarbonylamino-4-hydroxymethyl-pyrrolidine-1-carboxylate

benzyl (3S,4S)-3-tert-butoxycarbonylamino-4-methylsulfonyloxymethyl-pyrrolidine-1-carboxylate

Downstream raw materials:

(1R,5S)-tert-butyl 3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylate

Sofinicline

benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylate