(1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol

Base Information

• Chemical Name: (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol
• CAS No.: 141352-48-9
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.294
• Mol file: 141352-48-9.mol

Synonyms:(1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol

Chemical Property of (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol

There total 5 articles about (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol 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: 67.0%

(1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-carboxylic acid methyl ester (141352-47-8) → (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol (141352-48-9)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0957-4166(00)80286-4

Reference yield:

(-)-(1S,4R)-4-(acetylamino)-2-cyclopentene-1-carboxylic acid (112531-51-8) → (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol (141352-48-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 6 N aq. HCl / 4 h / Heating

2: 1.23 g / 2 N aq. NaOH / 2 h / Ambient temperature; pH 9

3: 50 percent / conc. HCl / 15 h / Ambient temperature

4: 67 percent / lithium triethyl borohydride / tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; sodium hydroxide; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1016/S0957-4166(00)80286-4

Reference yield:

ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique (61865-49-4,69919-17-1,86252-76-8,127061-46-5) → (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol (141352-48-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / H₂O / toluene / 35 °C / pH 7, pig liver esterase (PLE)

2: 6 N aq. HCl / 4 h / Heating

3: 1.23 g / 2 N aq. NaOH / 2 h / Ambient temperature; pH 9

4: 50 percent / conc. HCl / 15 h / Ambient temperature

5: 67 percent / lithium triethyl borohydride / tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; sodium hydroxide; water; lithium triethylborohydride; In tetrahydrofuran; toluene;

DOI:10.1016/S0957-4166(00)80286-4

upstream raw materials:

(1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-carboxylic acid methyl ester

(-)-(1S,4R)-4-(acetylamino)-2-cyclopentene-1-carboxylic acid

ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique

(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid