2-(Tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid

Base Information

• Chemical Name: 2-(Tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid
• CAS No.: 127926-24-3
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• Hs Code.: 2933990090
• European Community (EC) Number: 833-529-8
• Nikkaji Number: J1.803.381J
• Mol file: 127926-24-3.mol

Synonyms:127926-24-3;2-(tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid;2-[(tert-butoxy)carbonyl]-2-azabicyclo[2.1.1]hexane-1-carboxylic acid;2-Boc-2-aza-bicyclo[2.1.1]hexane-1-carboxylic acid;MFCD09040636;N-(t-butoxycarbonyl)-1-carboxy-2-azabicyclo[2.1.1]hexane;2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[2.1.1]hexane-1-carboxylic acid;2-Boc-2-azabicyclo[2.1.1]hexane-1-carboxylic acid;SCHEMBL14343401;SCHEMBL18116222;SCHEMBL22203883;ZCFGFDBKCBPYHR-UHFFFAOYSA-N;AKOS009118356;AKOS037644324;SB11894;(1s,4s)-2-[(tert-butoxy)carbonyl]-2-azabicyclo[2.1.1]hexane-1-carboxylic acid;AM803133;AS-50600;SY168358;CS-0037342;EN300-27230;P10681;EN300-6989192;Z237662918;2-(tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylicacid;2-Aza-bicyclo[2.1.1]hexane-1,2-dicarboxylic acid 2-tert-butyl ester

Chemical Property of 2-(Tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid

Chemical Property:

• Boiling Point: 347.8±25.0 °C(Predicted)
• PKA: 4.21±0.20(Predicted)
• PSA: 66.84000
• Density: 1.315±0.06 g/cm3(Predicted)
• LogP: 1.40840
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 338

Purity/Quality:

97% ^*data from raw suppliers

2-[(tert-butoxy)carbonyl]-2-azabicyclo[2.1.1]hexane-1-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC2CC1(C2)C(=O)O

Technology Process of 2-(Tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid

There total 5 articles about 2-(Tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid 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: 98.0%

carbon dioxide (124-38-9,18923-20-1) + tert-butyl 2-azabicyclo[2.1.1]hexane-2-carboxylate (467454-33-7) → 2-(tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid (127926-24-3)

Guidance literature:

tert-butyl 2-azabicyclo[2.1.1]hexane-2-carboxylate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at 0 ℃; for 2h;

carbon dioxide; In diethyl ether; cyclohexane; at 0 ℃; for 0.5h; Further stages.;

DOI:10.1021/ol026509b

Reference yield:

N-(benzyloxycarbonyl)-2-azabicyclo[2.1.1]hexane → 2-(tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid (127926-24-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 40 percent / hydrogen / Pd/C / methanol / 2 h / 20 °C / 760.05 Torr

2.1: sec-butyllithium; TMEDA / diethyl ether; cyclohexane / 2 h / 0 °C

2.2: 98 percent / diethyl ether; cyclohexane / 0.5 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; hydrogen; sec.-butyllithium; palladium on activated charcoal; In methanol; diethyl ether; cyclohexane;

DOI:10.1021/ol026509b

Reference yield:

methyl N-allyl-2-benzamidopropenoate (77422-37-8) → 2-(tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid (127926-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / acetophenone / benzene / 12 h / Ambient temperature; Irradiation

2: 98 percent / 6 N HCl / H₂O / 15 h / Heating

3: NaOH / H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; acetophenone; In water; tert-butyl alcohol; benzene;

DOI:10.1021/jo00255a024

upstream raw materials:

di-tert-butyl dicarbonate

2-azabicyclo[2.1.1]hexane-1-carboxylic acid

carbon dioxide

tert-butyl 2-azabicyclo[2.1.1]hexane-2-carboxylate

Downstream raw materials:

N-(t-butoxycarbonyl)-1-carbomethoxy-2-azabicyclo[2.1.1]hexane

Cis-ACBD

methyl 2,4-methanopyroglutamate

cis-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid