trans-4-Fluoroproline

Base Information

• Chemical Name: trans-4-Fluoroproline
• CAS No.: 2507-61-1
• Molecular Formula: C₅H₈FNO₂
• Molecular Weight: 133.122
• Hs Code.: 2933998090
• Mol file: 2507-61-1.mol

Synonyms:TRANS-4-FLUOROPROLINE;(2S,4R)-4-Fluoropyrrolidinium-2-carboxylate;(2S,4R)-4-FLUOROPYRROLIDIN-1-IUM-2-CARBOXYLATE

Chemical Property of trans-4-Fluoroproline

Chemical Property:

• Appearance/Colour: Colourless solid
• Vapor Pressure: 0.00271mmHg at 25°C
• Melting Point: 264°C(lit.)
• Refractive Index: 1.472
• Boiling Point: 265.108 °C at 760 mmHg
• PKA: 1.88±0.40(Predicted)
• Flash Point: 114.133 °C
• PSA: 49.33000
• Density: 1.309 g/cm³
• LogP: 0.09980
• Storage Temp.: Store at RT.
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 133.05390666
• Heavy Atom Count: 9
• Complexity: 123

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-4-Fluoropyrrolidine-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C[NH2+]C1C(=O)[O-])F
• Isomeric SMILES: C1[C@H](C[NH2+][C@@H]1C(=O)[O-])F

Technology Process of trans-4-Fluoroproline

There total 9 articles about trans-4-Fluoroproline 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: 58.0%

(5S,7R)-7-fluoro-2,2-bis(trifluoromethyl)-1-aza-3-oxabicyclo<3.3.0>octan-4-one (156046-04-7) → (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid (2438-57-5,2507-61-1,7553-49-3,21156-44-5,21156-75-2,60828-35-5,131176-02-8,913820-71-0)

Guidance literature:

With water; In isopropyl alcohol; Ambient temperature;

DOI:10.1016/0022-1139(93)02907-V

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid (2438-57-5,2507-61-1,7553-49-3,21156-44-5,21156-75-2,60828-35-5,131176-02-8,913820-71-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / Et₃N / CHCl₃ / 0 °C

2: 1.) PPh₃, DEAD, PhCO₂H; 2.) KOH / 1.) toluene; 2.) MeOH

3: 63 percent / DAST / CH₂Cl₂ / -78 deg C to r.t.

4: 99 percent / LiOH / acetonitrile; H₂O / Ambient temperature

5: TFA / CH₂Cl₂

With potassium hydroxide; lithium hydroxide; triethylamine; triphenylphosphine; 4,4'-diaminostilbene-2,2'-disulfonic acid; benzoic acid; trifluoroacetic acid; diethylazodicarboxylate; In dichloromethane; chloroform; water; acetonitrile;

DOI:10.1016/S0040-4039(97)10793-6

Reference yield:

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid (203866-14-2) → (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid (2438-57-5,2507-61-1,7553-49-3,21156-44-5,21156-75-2,60828-35-5,131176-02-8,913820-71-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4039(97)10793-6

upstream raw materials:

(5S,7R)-7-fluoro-2,2-bis(trifluoromethyl)-1-aza-3-oxabicyclo<3.3.0>octan-4-one

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid

(6S,7aS)-6-hydroxy-3,3-bis(trifluoromethyl)tetrahydro-pyrrolo[1,2-c]oxazol-1-one

hydroxy L-proline

Downstream raw materials:

(2S,4R)-N-Fmoc-4-fluoroproline

(2S,4R)-N-methyl-4-fluoropyrrolidine-2-carboxylic acid hydrochloride

1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-{(1S,4R)-4-[3-((2S,4R)-4-fluoro-1-methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea