(2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid
• CAS No.: 203866-13-1
• Molecular Formula: C10H16FNO4
• Molecular Weight: 233.24
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID4049242
• Nikkaji Number: J932.817C
• Wikidata: Q72449298
• ChEMBL ID: CHEMBL3187987
• Mol file: 203866-13-1.mol

Synonyms:203866-13-1;N-Boc-cis-4-fluoro-L-proline;(2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid;(2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoro-2-pyrrolidinecarboxylic Acid;(2S,4S)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid;(2S,4S)-4-fluoro-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;DTXSID4049242;(4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline;MFCD04973957;C10H16FNO4;(2S,4S)-4-FLUORO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;BOC-CIS-PRO(4-F)-OH;N-tert-butoxycarbonyl-cis-4-fluoro-L-proline;1-(tert-butoxycarbonyl)-4-fluoroproline;BOC-CIS-4-FLUORO-L-PROLINE;(2S,4S)-4-Fluoro-N-Boc-Pyrrolidine-2-carboxylic acid;boc-4-(s)-fluoroproline;cis-Boc-4-F-L-Pro-OH;SCHEMBL192921;(2S,4S)-1-Boc-4-fluoro-2-pyrrolidinecarboxylic Acid;CHEMBL3187987;DTXCID6029098;YGWZXQOYEBWUTH-BQBZGAKWSA-N;(2S,4S)-BOC-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID;N-tert-Boc-cis-4-fluoro-L-proline;Tox21_202813;AKOS005063318;AKOS015892910;N-Boc-cis-4-fluoro-L-proline, 97%;CS-W003222;NCGC00260359-01;DS-16680;A4435;AM20090156;B3178;BB 0260227;CAS-203866-13-1;(4s)-n-tert-butoxycarbonyl-4-fluoro-l-proline;EN300-259444;N-tert-Butoxycarbonyl-(2S,4S)-4-fluoroproline;N-(tert-Butoxycarbonyl)-cis-4-fluoro-L-proline;(4S)-1-(tert-butoxycarbonyl)-4-fluoro-L-proline;AU-004/43497116;(4S)-1-(tert-butoxy carbonyl)-4-fluoro-L-proline;Q-103492;(2S,4S)-N-Boc-4-fluoropyrrolidine-2-carboxylic acid;(2S,4S)-1-(Boc)-4-fluoropyrrolidine-2-carboxylic acid;(2S,4S)-1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid;(4S)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-fluoro-L-proline;cis-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid;(2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylicacid;1,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) ester, (2S,4S)-

Chemical Property of (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.05E-05mmHg at 25°C
• Melting Point: 157-161 °C
• Refractive Index: -57 ° (C=1, MeOH)
• Boiling Point: 346 °C at 760 mmHg
• PKA: 3.53±0.40(Predicted)
• Flash Point: 163 °C
• PSA: 66.84000
• Density: 1.24 g/cm³
• LogP: 1.35640
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 233.10633615
• Heavy Atom Count: 16
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

Boc-cis-4-fluoro-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)F
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)O)F
• Uses: N-Boc-cis-4-fluoro-L-proline can be used as a substrate in the preparation of:α4β2 Receptor ligands bearing pyrrolidine nucleus.β-Amino pyrrolidine-2-carbonitrile derivatives as possible dipeptidyl peptidase IV (DPP4) inhibitors.

Technology Process of (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

There total 15 articles about (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-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: 96.0%

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4) → (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-13-1)

Guidance literature:

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With water; lithium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

With hydrogenchloride; In water; pH=5;

Reference yield: 72.0%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-13-1)

Guidance literature:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate; With diethylamino-sulfur trifluoride; In dichloromethane; at -15 - 20 ℃; for 4h;

With water; sodium hydroxide; at 40 ℃; for 3h; Reagent/catalyst; Solvent; Temperature;

DOI:10.1021/acs.oprd.0c00080

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-13-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: 81 percent / DAST / CH₂Cl₂ / -78 deg C to r.t.

3: 92 percent / LiOH / acetonitrile; H₂O / Ambient temperature

With lithium hydroxide; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; water; acetonitrile;

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

upstream raw materials:

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate

N-tert-butoxycarbonyl-(2S,4S)-4-fluoroproline benzyl ester

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

Downstream raw materials:

(2S,4S)-4-fluoropyrrolidine-2-carboxylic acid

C₁₈H₂₁BrFN₃O₂

C₂₄H₃₃BFN₃O₄

C₃₀H₃₁F₄N₃O₅S

Refernces

• 1、 -. "West request acid bei geleg sandbank and intermediate preparation method". Paragraph 0100-0104. . Retrieved 2019/02/26.
• 2、 -. "As hepatitis c inhibitor spiro compound and its use in medicine". Paragraph 1003; 1008; 1009. . Retrieved 2017/12/28.