(1S,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester
• CAS No.: 262280-14-8
• Molecular Formula: C₁₂H₂₁NO₅
• Molecular Weight: 259.302
• Hs Code.: 29221985
• DSSTox Substance ID: DTXSID20427437
• Nikkaji Number: J1.562.825A
• Wikidata: Q82240095
• Mol file: 262280-14-8.mol

Synonyms:262280-14-8;(1S,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester;(1R,3S,4S)-Methyl 3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate;methyl (1R,3S,4S)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate;methyl (1R,3S,4S)-3-{[(tert-butoxy)carbonyl]amino}-4-hydroxycyclopentane-1-carboxylate;Cyclopentanecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-, methyl ester, (1R,3S,4S)-;SCHEMBL3546943;DTXSID20427437;MFCD02259721;BS-42766;CS-0049306;P17295;Methyl (1R,3S,4S)-3-(Boc-amino)-4-hydroxycyclopentane-1-carboxylate;(1R,3S,4S)-Methyl3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate;Methyl (1R,3S,4S)-3-[(t-butoxy)carbonyl]amino-4-hydroxycyclopentane-1-carboxylate;(1R,3S,4S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-hydroxycyclopentanecarboxylic Acid Methyl Ester;3alpha-[(tert-Butyloxycarbonyl)amino]-4beta-hydroxycyclopentane-1alpha-carboxylic acid methyl ester;METHYL (1R,3S,4S)-3-{[(TERT-BUTOXY)CARBONYL]AMINO-4-HYDROXYCYCLOPENTANE-1-CARBOXYLATE

Chemical Property of (1S,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester

Chemical Property:

• Vapor Pressure: 2.9E-07mmHg at 25°C
• Refractive Index: 1.4596 (estimate)
• Boiling Point: 378°Cat760mmHg
• Flash Point: 182.4°C
• PSA: 84.86000
• Density: 1.16g/cm³
• LogP: 1.21450
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 259.14197277
• Heavy Atom Count: 18
• Complexity: 323

Purity/Quality:

97% ^*data from raw suppliers

(1R,3S,4S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-hydroxycyclopentanecarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CC(CC1O)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H]1C[C@H](C[C@@H]1O)C(=O)OC
• Uses: (1R,3S,4S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-hydroxycyclopentanecarboxylic Acid Methyl Ester is used in the synthesis of potent inactivators of γ-aminobutyric acid aminotransferase.

Technology Process of (1S,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester

There total 15 articles about (1S,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester 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: 95.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (1R,3S,4S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxycyclopentane-1-carboxylic acid (262280-12-6) → (1S,2S,4R)-1-(tert-butoxycarbonylamino)-2-hydroxycyclopentane-4-carboxylic acid methyl ester (262280-14-8,321744-18-7)

Guidance literature:

In methanol; diethyl ether;

DOI:10.1021/jm9904755

Reference yield:

(1R,3S,4R)-3-tert-Butoxycarbonylamino-4-methanesulfonyloxy-cyclopentanecarboxylic acid methyl ester → (1S,2S,4R)-1-(tert-butoxycarbonylamino)-2-hydroxycyclopentane-4-carboxylic acid methyl ester (262280-14-8,321744-18-7)

Guidance literature:

(1R,3S,4R)-3-tert-Butoxycarbonylamino-4-methanesulfonyloxy-cyclopentanecarboxylic acid methyl ester; With potassium acetate; In N,N-dimethyl-formamide; at 60 ℃; for 72h;

With sodium methylate; In methanol; at 0 ℃; for 7h; Further stages.;

DOI:10.1016/j.tet.2003.10.116

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (1S,2S,4R)-1-(tert-butoxycarbonylamino)-2-hydroxycyclopentane-4-carboxylic acid methyl ester (262280-14-8,321744-18-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: KOH / H₂O; methanol / 48 h / 90 °C

1.2: tetrahydrofuran; H₂O / 14 h / 20 °C / pH 10.5

2.1: H₂ / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr

3.1: triethylamine / methanol / 5 - 20 °C

4.1: triethylamine; DMAP / CH₂Cl₂ / 0.75 h / 0 °C

5.1: KOAc / dimethylformamide / 72 h / 60 °C

5.2: NaOMe / methanol / 7 h / 0 °C

With dmap; potassium hydroxide; hydrogen; potassium acetate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2003.10.116

upstream raw materials:

diazomethane

(1R,3S,4S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxycyclopentane-1-carboxylic acid

di-tert-butyl dicarbonate

(1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester