910787-06-3

Basic information

• Product Name: (+)-B-((9-(1S,2S)-N-methylpseudoephedrinyl)-(10S)-phenyl-9-borabicyclo-[3.3.2]decane)
• Synonyms: (+)-B-((9-(1S,2S)-N-methylpseudoephedrinyl)-(10S)-phenyl-9-borabicyclo-[3.3.2]decane)
• CAS NO: 910787-06-3
• Molecular Weight: 389.389
• Mol File: 910787-06-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+)-B-((9-(1S,2S)-N-methylpseudoephedrinyl)-(10S)-phenyl-9-borabicyclo-[3.3.2]decane)(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-B-((9-(1S,2S)-N-methylpseudoephedrinyl)-(10S)-phenyl-9-borabicyclo-[3.3.2]decane)(910787-06-3)
• EPA Substance Registry System: (+)-B-((9-(1S,2S)-N-methylpseudoephedrinyl)-(10S)-phenyl-9-borabicyclo-[3.3.2]decane)(910787-06-3)

Safety Data

• Hazardous Substances Data: 910787-06-3(Hazardous Substances Data)

Upstream product

• 865358-58-3 (+)-(1S)-B-allyl-10-phenyl-9-borabicyclo[3.3.2]decane 
• 38050-71-4 9-methoxy-9-BBN 
• 908094-04-2 phenyldiazomethane 
• 865358-55-0 (±)-B-methoxy-10-phenyl-9-borabicyclo[3.3.2]decane 
• 1201-56-5 (1S,2S)-N-Methylpseudoephedrine 
• 14222-20-9 1R,2R-N-methylpseudoephedrine 

Downstream Products

• 910787-09-6 (S)-B-allenyl-10-phenyl-9-borabicyclo[3.3.2]decane 
• 865358-58-3 (+)-(1S)-B-allyl-10-phenyl-9-borabicyclo[3.3.2]decane 

Relevant articles and documents

Nonracemic 3°-carbamines from the asymmetric allylboration of N-trimethylsilyl ketimines with B-allyl-10-phenyl-9-borabicyclo[3.3.2]decanes

The simple and efficient asymmetric synthesis of 3°-carbamines 7 from N-TMS enamines (3) and either enantiomeric form of β-allyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) is reported. The high reactivity (1 h, -78 °C) and enantioselectivity (60-98% ee) of these substrates can be attributed to the fact that the complexation of 3 with 1 facilitates its isomerization to the corresponding syn-N-TMS ketimine complex from which allylation can occur. In addition to providing the homoallylic amines 7 with predictable stereochemistry, the procedure also permits the efficient recovery of the chiral boron moiety (50-65%) as air-stable crystalline pseudoephedrine complexes 8, which are directly converted back to 1 with allylmagnesium bromide in ether (98%). Copyright