(1S,2S)-N-Methyl-1-phenyl-1-{[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-amine

Base Information

• Chemical Name: (1S,2S)-N-Methyl-1-phenyl-1-{[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-amine
• CAS No.: 848618-13-3
• Molecular Formula: C22H38 B N O Si
• Molecular Weight: 371.446
• European Community (EC) Number: 624-845-5
• DSSTox Substance ID: DTXSID70584867
• Nikkaji Number: J2.195.507H
• Wikidata: Q76511219
• Mol file: 848618-13-3.mol

Synonyms:848618-13-3;DTXSID70584867;(+)-9-(1S, 2S-Pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane;(+)-9-(1s,2s-Pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane;(1S,2S)-N-Methyl-1-phenyl-1-{[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-amine

Chemical Property of (1S,2S)-N-Methyl-1-phenyl-1-{[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-amine

Chemical Property:

• Vapor Pressure: 2.31E-08mmHg at 25°C
• Melting Point: 130-134 °C
• Refractive Index: 1.5
• Boiling Point: 452.1°C at 760 mmHg
• Flash Point: 227.2°C
• PSA: 21.26000
• Density: 0.95g/cm³
• LogP: 6.33640
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 371.2815715
• Heavy Atom Count: 26
• Complexity: 424

Purity/Quality:

97% ^*data from raw suppliers

(+)-9-(1S, 2S-PSEUDOEPHEDRINYL)-(10R)-(TRIMETHYLSILYL)-9-BORABICYCLO[3.3.2]DECANE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(C2CCCC(C1[Si](C)(C)C)CCC2)OC(C3=CC=CC=C3)C(C)NC
• Isomeric SMILES: B1([C@H](C2CCCC1CCC2)[Si](C)(C)C)O[C@@H](C3=CC=CC=C3)[C@H](C)NC

Technology Process of (1S,2S)-N-Methyl-1-phenyl-1-{[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-amine

There total 7 articles about (1S,2S)-N-Methyl-1-phenyl-1-{[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-amine 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: 71.0%

(R)-9-(1-Methyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane + pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) → 9-(1S,2S-pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane (848618-13-3) + (-)-(2S)-3-(trimethylsilyl)-3,4-pentadien-2-ol (135758-81-5) + (+)-(2R)-3-(trimethylsilyl)-3,4-pentadien-2-ol (173654-25-6)

Guidance literature:

In acetonitrile; at 81 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1021/ol051886k

Reference yield: 38.0%

(+/-)-B-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2]decane (848617-93-6) + pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) → 9-(1S,2S-pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane (848618-13-3)

Guidance literature:

In acetonitrile; for 6h; Heating;

DOI:10.1021/ja043612i

Reference yield:

(R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane (872359-75-6) + pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) → 9-(1S,2S-pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane (848618-13-3) + (-)-(1S)-1-phenyl-2-(trimethylsilyl)-2,3-butadien-1-ol (872420-37-6)

Guidance literature:

In acetonitrile; at 81 ℃; for 15h;

DOI:10.1021/ol051886k

upstream raw materials:

(+/-)-B-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2]decane

pseudoephedrine

(R)-9-((S)-1-Propyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane

(R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane

Downstream raw materials:

(-)-(1S)-1-phenyl-2-(trimethylsilyl)-2,3-butadien-1-ol

(S)-Mandelic acid

C₁₁H₁₆O₃Si

(S)-2-Hydroxy-2-phenyl-1-trimethylsilanyl-ethanone