dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene

Base Information

• Chemical Name: dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene
• CAS No.: 113007-97-9
• Molecular Formula: C₁₃H₁₅NO₃S
• Molecular Weight: 265.333
• Mol file: 113007-97-9.mol

Synonyms:dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene

Chemical Property of dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene

There total 9 articles about dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene 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: 64.0%

dl-cis-2-<2-<(phenylsulfonyl)amino>cyclopent-4-enyl>ethanol (113007-95-7) → dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene (113007-97-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 0.25h;

DOI:10.1021/jm00163a038

Reference yield:

1-hydroxy-2-(2-hydroxyethyl)cyclopent-3-ene (49826-08-6,54483-54-4,54483-55-5,75331-67-8) → dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene (113007-97-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / Ambient temperature

2: 40.9 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 0.25 h / Ambient temperature

3: 95 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 5 h / Heating

4: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: NaN₃ / dimethylformamide / 5 h / 75 °C

6: 1.) Ph₃P, 2.) H₂O / 1.) RT, 15 h, 2.) a.) 45 deg C, 2 h, b.) reflux, 1 h

7: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

9: 64 percent / oxalyl chloride/DMSO / CH₂Cl₂ / 0.25 h / -60 °C

With hydrogenchloride; dmap; sodium azide; oxalyl dichloride; water; sodium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00163a038

Reference yield:

dl-trans-2-<2-(benzoyloxy)cyclopent-4-enyl>ethanol triphenylmethyl ether (112918-26-0) → dl-(1α,5α)-2-(phenylsulfonyl)-3-hydroxy-2-azabicyclo<3.3.0>oct-6-ene (113007-97-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 5 h / Heating

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: NaN₃ / dimethylformamide / 5 h / 75 °C

4: 1.) Ph₃P, 2.) H₂O / 1.) RT, 15 h, 2.) a.) 45 deg C, 2 h, b.) reflux, 1 h

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

7: 64 percent / oxalyl chloride/DMSO / CH₂Cl₂ / 0.25 h / -60 °C

With hydrogenchloride; sodium azide; oxalyl dichloride; water; sodium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00163a038

upstream raw materials:

dl-cis-2-<2-<(phenylsulfonyl)amino>cyclopent-4-enyl>ethanol

1-hydroxy-2-(2-hydroxyethyl)cyclopent-3-ene

dl-trans-2-<2-(benzoyloxy)cyclopent-4-enyl>ethanol triphenylmethyl ether

dl-cis-2-(2-aminocyclopent-4-enyl)ethanol triphenylmethyl ether

Downstream raw materials:

dl-(1β,5β)-2-(phenylsulfonyl)-3-hydroxy-6β,7β-epoxy-2-azabicyclo<3.3.0>octane

dl-methyl (1α,2α,3α,5α)-7-<3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

(Z)-7-((1R,2S,3S)-3-Benzenesulfonylamino-6-oxa-bicyclo[3.1.0]hex-2-yl)-hept-5-enoic acid