4-amino-5-chloro-N-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-2-methoxybenzamide

Base Information

• Chemical Name: 4-amino-5-chloro-N-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-2-methoxybenzamide
• CAS No.: 141196-99-8
• Molecular Formula: C16H22 Cl N3 O2
• Molecular Weight: 323.823
• Mol file: 141196-99-8.mol

Synonyms:Benzamide,4-amino-5-chloro-N-[(hexahydro-1H-pyrrolizin-1-yl)methyl]-2-methoxy-,(1S-cis)-; SC 53116

Chemical Property of 4-amino-5-chloro-N-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-2-methoxybenzamide

Chemical Property:

• Vapor Pressure: 6E-09mmHg at 25°C
• Boiling Point: 468.4°C at 760 mmHg
• Flash Point: 237.1°C
• PSA: 71.08000
• Density: 1.3g/cm³
• LogP: 3.23880
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble10mg/mL, clear

Purity/Quality:

99% ^*data from raw suppliers

SC-53116 hydrochloride hydrate ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-amino-5-chloro-N-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-2-methoxybenzamide

There total 18 articles about 4-amino-5-chloro-N-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-2-methoxybenzamide 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: 88.0%

4-Amino-5-chloro-N-[(2S,3S)-5-[1,3]dioxolan-2-yl-2-[1,3]dioxolan-2-ylmethyl-3-((R)-2-methyl-propane-2-sulfinylamino)-pentyl]-2-methoxy-benzamide (781658-60-4) → 4-amino-5-chloro-N-[(hexahydro-1H-pyrrolizin-1-yl)methyl]-2-methoxybenzamide (141196-99-8)

Guidance literature:

With hydrogen; trifluoroacetic acid; platinum(IV) oxide; In ethanol; water; at 40 ℃; for 17h;

DOI:10.1021/ol048458j

Reference yield:

2-Methyl-propane-2-sulfinic acid [(1S,2R)-2-cyano-3-[1,3]dioxolan-2-yl-1-(2-[1,3]dioxolan-2-yl-ethyl)-propyl]-amide (781658-58-0) → 4-amino-5-chloro-N-[(hexahydro-1H-pyrrolizin-1-yl)methyl]-2-methoxybenzamide (141196-99-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / BH₃*SMe₂ / tetrahydrofuran / 3.5 h / 70 °C

2.1: 1-hydroxybenzotriazole hydrate; 1,3-dicyclohexylcarbodiimide / dimethylformamide / 0.17 h

2.2: 80 percent / dimethylformamide / 16 h / 20 °C

3.1: 88 percent / H₂; trifluoroacetic acid / PtO₂ / ethanol; H₂O / 17 h / 40 °C

With dimethylsulfide borane complex; hydrogen; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; trifluoroacetic acid; platinum(IV) oxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ol048458j

Reference yield:

2-Methyl-propane-2-sulfinic acid [(1S,2S)-2-aminomethyl-3-[1,3]dioxolan-2-yl-1-(2-[1,3]dioxolan-2-yl-ethyl)-propyl]-amide (781658-59-1) → 4-amino-5-chloro-N-[(hexahydro-1H-pyrrolizin-1-yl)methyl]-2-methoxybenzamide (141196-99-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-hydroxybenzotriazole hydrate; 1,3-dicyclohexylcarbodiimide / dimethylformamide / 0.17 h

1.2: 80 percent / dimethylformamide / 16 h / 20 °C

2.1: 88 percent / H₂; trifluoroacetic acid / PtO₂ / ethanol; H₂O / 17 h / 40 °C

With hydrogen; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; trifluoroacetic acid; platinum(IV) oxide; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ol048458j

upstream raw materials:

4-(acetylamino)-5-chloro-2-methoxybenzoic acid

(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethylamine

4-Amino-5-chloro-N-[(2S,3S)-5-[1,3]dioxolan-2-yl-2-[1,3]dioxolan-2-ylmethyl-3-((R)-2-methyl-propane-2-sulfinylamino)-pentyl]-2-methoxy-benzamide

2-[(1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-1H-isoindole-1,3(2H)-dione

Refernces

• 1、 Schenkel, Laurie B.,Ellman, Jonathan A.. "Self-condensation of N-tert-butanesulfinyl aldimines: Application to the rapid asymmetric synthesis of biologically important amine-containing compounds". . p. 3621 - 3624. Retrieved 2007/10/03.