Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, cis- (9CI)

Base Information

• Chemical Name: Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, cis- (9CI)
• CAS No.: 109794-96-9
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.158
• Mol file: 109794-96-9.mol

Synonyms:Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, cis- (9CI)

Chemical Property of Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, cis- (9CI)

Chemical Property:

• Boiling Point: 326.2±17.0 °C(Predicted)
• PKA: 2.26±0.40(Predicted)
• PSA: 83.55000
• Density: 1.346±0.06 g/cm3(Predicted)
• LogP: -0.12890

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, cis- (9CI)

There total 10 articles about Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, cis- (9CI) 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: 97.0%

methyl cis-1-<(tert-butyloxycarbonyl)amino>-3-(hydroxymethyl)cyclobutanecarbxylate (116129-03-4) → cis-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid (109794-96-9,1555492-59-5)

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; for 3h;

DOI:10.1021/jo00255a024

Reference yield: 78.0%

3-hydroxymethyl-cyclobutane-1,1-dicarboxylic acid monohydrazide (116823-34-8) → cis-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid (109794-96-9,1555492-59-5)

Guidance literature:

With hydrogenchloride; sodium nitrite; In diethyl ether; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)90351-5

Reference yield:

methyl N-allyl-2-benzamidopropenoate (77422-37-8) → cis-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid (109794-96-9,1555492-59-5)

Guidance literature:

Multi-step reaction with 7 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

4: CH₂Cl₂

5: 66 percent / sodium m-periodate, ruthenium dioxide / acetonitrile; H₂O; CCl₄ / 504 h

6: 91 percent / borane / tetrahydrofuran / 0.25 h / 0 °C

7: 97 percent / 1 N HCl / H₂O / 3 h / 80 °C

With hydrogenchloride; ruthenium(IV) oxide; sodium hydroxide; sodium periodate; borane; acetophenone; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1021/jo00255a024

upstream raw materials:

3-hydroxymethyl-cyclobutane-1,1-dicarboxylic acid monohydrazide

methyl cis-1-<(tert-butyloxycarbonyl)amino>-3-(hydroxymethyl)cyclobutanecarbxylate

cis-1-(benzoylamino)-3-(hydroxymethyl)cyclobutane-1-N,N-pentamethylenecarboxamide

methyl N-allyl-2-benzamidopropenoate

Refernces

• 1、 Gaoni, Yehiel. "SYNTHESIS OF AMINOCYCLOBUTANE MONO- AND DICARBOXYLIC ACIDS AND DERIVATIVES THEREOF FROM (PHENYLSULFONYL)BICYCLOBUTANES". . p. 185 - 212. Retrieved 2007/10/02.