96228-13-6

Basic information

• Product Name: (1S,2R)-2-Isopropylideneamino-1-phenyl-propan-1-ol
• Synonyms: (1S,2R)-2-Isopropylideneamino-1-phenyl-propan-1-ol
• CAS NO: 96228-13-6
• Molecular Weight: 191.273
• Mol File: 96228-13-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1S,2R)-2-Isopropylideneamino-1-phenyl-propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-Isopropylideneamino-1-phenyl-propan-1-ol(96228-13-6)
• EPA Substance Registry System: (1S,2R)-2-Isopropylideneamino-1-phenyl-propan-1-ol(96228-13-6)

Safety Data

• Hazardous Substances Data: 96228-13-6(Hazardous Substances Data)

Upstream product

• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 67-64-1 acetone 
• 120443-82-5 (R)-2-phenyl-2-(trimethylsiloxy)acetonitrile 
• 10020-96-9 (R)-Mandelonitrile 
• 492-41-1 (1R,2S)-norephedrine 

Downstream Products

• 190442-40-1 (1S,2R)-2-(isopropylamino)-1-phenylpropan-1-ol 
• 161860-15-7 (2R,3R,4S,5R)-2-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-3-isopropyl-4-methyl-5-phenyl-[1,3,2]oxazaphospholidine 2-sulfide 
• 161860-14-6 (2S,3R,4S,5R)-2-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-3-isopropyl-4-methyl-5-phenyl-[1,3,2]oxazaphospholidine 
• 161860-13-5 (2R,3R,4S,5R)-2-Chloro-3-isopropyl-4-methyl-5-phenyl-[1,3,2]oxazaphospholidine 
• 652155-36-7 (4R,5S,6R)-3,4,5,6-tetrahydro-3-[(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl]-4-isopropyl-5-methyl-6-phenyl-2H-1,3,4-oxadiazin-2-one 
• 652155-35-6 (4R,5S,6R)-4-isopropyl-5-methyl-6-phenyl-3-[3-(phenylthio)propionyl]-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one 

Relevant articles and documents

Stereoselective synthesis of (1R)- and (1R,2S)-1-aryl-2-alkylamino alcohols from (R)-cyanohydrins

Hydrogenation of (R)-cyanohydrins (R)-1 with LiAlH4 occurs without racemization to give the (R)-2-amino alcohols (R)-3. (1R,2S)-2-Amino alcohols (1R,2S)-4 are obtained with high diastereoselectivity by addition of methyl Grignard to O-silyl protected cyanohydrins (R)-2 and subsequent hydrogenation with NaBH4. The N-alkylated 2-amino alcohols (R)-8 and (1R,2S)-9 can be prepared either by reductive alkylation of the corresponding 2-amino alcohols (R)-3 and (1R,2S)-4, respectively, or by a transimination reaction of the Grignard addition products with primary amines and subsequent hydrogenation with NaBH4. The lower diastereoselectivity of hydrogenation in case of the N-alkylmino compounds in comparison to the N-unsubstituted imines is explained by a weaker chelating effect.

Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: Scope and limitations

Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such as SOCl2, TsCl, or AcCl. The intramolecular trapping of the activated carbamate by a hydroxyl group leads to the formation of 2-oxazolidinones or 2-oxazinones in good to excellent yields. This methodology was successfully applied to the synthesis of cyclic ureas up to 7-membered rings from the corresponding diamines.

Intramolecular Chiral Relay at Stereogenic Nitrogen. Synthesis and Application of A New Chiral Auxiliary Derived from (1R,2S)-Norephedrine and Acetone

(1R,2S)-Norephedrine has been employed in the synthesis of a novel 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one via reductive alkylation with acetone, N-nitrosation, reduction, and cyclization. The oxadiazinone was treated with either propionyl chloride or