(1S,3S,4R)-Methyl 3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate

Base Information

• Chemical Name: (1S,3S,4R)-Methyl 3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate
• CAS No.: 321744-21-2
• Molecular Formula: C₁₂H₂₁NO₅
• Molecular Weight: 259.302
• Hs Code.: 29221985
• DSSTox Substance ID: DTXSID50427440
• Nikkaji Number: J1.562.826J
• Wikidata: Q82240101
• Mol file: 321744-21-2.mol

Synonyms:321744-21-2;(1S,3S,4R)-Methyl 3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate;methyl (1S,3R,4S)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate;DTXSID50427440;(1S,2R,4S)-N-BOC-1-AMINO-2-HYDROXYCYCLOPENTANE-4-CARBOXYLIC ACID METHYL ESTER;(1S,2R,4S)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester, AldrichCPR;(1S,3S,4R)-Methyl3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate;Methyl (1S,3S,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxycyclopentane-1-carboxylate;3alpha-[(tert-Butyloxycarbonyl)amino]-4alpha-hydroxycyclopentane-1beta-carboxylic acid methyl ester

Chemical Property of (1S,3S,4R)-Methyl 3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate

Chemical Property:

• Vapor Pressure: 2.9E-07mmHg at 25°C
• Refractive Index: 1.4596 (estimate)
• Boiling Point: 378°Cat760mmHg
• PKA: 11.62±0.60(Predicted)
• 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:

98%Min ^*data from raw suppliers

(1S,2R,4S)-N-BOC-1-AMINO-2-HYDROXYCYCLOPENTANE-4-CARBOXYLIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• 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

Technology Process of (1S,3S,4R)-Methyl 3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate

There total 9 articles about (1S,3S,4R)-Methyl 3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentanecarboxylate 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:

(3R,4S)-4-tert-butoxycarbonylamino-3-hydroxycyclopent-1-enecarboxylic acid methyl ester (329910-37-4) → (1S,3S,4R)-3-tert-butoxycarbonylamino-4-hydroxycyclopentanecarboxylic acid methyl ester (321744-21-2,321744-18-7)

Guidance literature:

With 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; In methanol; at 20 ℃; under 3878.61 Torr;

DOI:10.1016/S0957-4166(01)00108-2

Reference yield:

(1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester (251326-99-5) → (1S,3S,4R)-3-tert-butoxycarbonylamino-4-hydroxycyclopentanecarboxylic acid methyl ester (321744-21-2,321744-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-bromosuccinimide / tetrahydrofuran; H₂O / 17 h / 20 °C

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

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

3.1: triethylamine / methanol / 16 h / 0 - 20 °C

4.1: H₂ / [(S,S)-(Me-DuPHOS)-Rh(COD)]BF₄ / methanol / 14 h / 20 °C / 3750.38 Torr

With potassium hydroxide; N-Bromosuccinimide; hydrogen; triethylamine; (Z,Z)-cycloocta-1,5-diene(S,S-1,2-bis(2,5-dimethylphospholanyl)benzene)rhodium(I) tetrafluoroborate; In tetrahydrofuran; methanol; water;

DOI:10.1016/j.tet.2003.10.116

Reference yield:

(3R,4S)-4-tert-butoxycarbonylamino-3-hydroxycyclopent-1-enecarboxylic acid (329910-36-3) → (1S,3S,4R)-3-tert-butoxycarbonylamino-4-hydroxycyclopentanecarboxylic acid methyl ester (321744-21-2,321744-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / methanol / 16 h / 0 - 20 °C

2: H₂ / [(S,S)-(Me-DuPHOS)-Rh(COD)]BF₄ / methanol / 14 h / 20 °C / 3750.38 Torr

With hydrogen; triethylamine; (Z,Z)-cycloocta-1,5-diene(S,S-1,2-bis(2,5-dimethylphospholanyl)benzene)rhodium(I) tetrafluoroborate; In methanol;

DOI:10.1016/j.tet.2003.10.116

upstream raw materials:

(3R,4S)-4-tert-butoxycarbonylamino-3-hydroxycyclopent-1-enecarboxylic acid methyl ester

di-tert-butyl dicarbonate

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

(3R,4S)-4-tert-butoxycarbonylamino-3-hydroxycyclopent-1-enecarboxylic acid

Downstream raw materials:

(1S,2S,4S)-1-(tert-butoxycarbonylamino)-2-hydroxycyclopentane-4-carboxylic acid methyl ester