158690-57-4

Basic information

• Product Name: (7aS)-tetrahydro-1H,3H-Pyrrolo[1,2-c]oxazol-3-one
• Synonyms: (7aS)-tetrahydro-1H,3H-Pyrrolo[1,2-c]oxazol-3-one
• CAS NO: 158690-57-4
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.14116
• Mol File: 158690-57-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 316.9±9.0 °C(Predicted)
• Appearance: /
• Density: 1.25±0.1 g/cm3(Predicted)
• PKA: -1.40±0.20(Predicted)
• CAS DataBase Reference: (7aS)-tetrahydro-1H,3H-Pyrrolo[1,2-c]oxazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (7aS)-tetrahydro-1H,3H-Pyrrolo[1,2-c]oxazol-3-one(158690-57-4)
• EPA Substance Registry System: (7aS)-tetrahydro-1H,3H-Pyrrolo[1,2-c]oxazol-3-one(158690-57-4)

Safety Data

• Hazardous Substances Data: 158690-57-4(Hazardous Substances Data)

Upstream product

• 68832-13-3 D-prolinol 
• 105-58-8 Diethyl carbonate 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 616-38-6 carbonic acid dimethyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 147-85-3 L-proline 
• 192456-74-9 (S)-tetrahydropyrrolo[1,2-c]oxazole-3(1H)-thione 
• 530-62-1 1,1'-carbonyldiimidazole 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 1004-09-7 (rac)-sodium 1-phenylethanolate 
• 201230-82-2 carbon monoxide 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 

Downstream Products

• 173290-25-0 (R)-2-hydroxymethyl-N-(3-phenyl-2-propynoyl)pyrrolidine 

Relevant articles and documents

Loss of the tert-butyloxycarbonyl (Boc) protecting group under basic conditions

Reaction of 3, the N-Boc, O-tosyl derivative of phenylalaninol, with base leads to loss of the Boc and tosyl groups and formation of oxazolidinone 9. Similar reactions have also been examined. A mechanism to explain loss of the Boc group under basic reaction conditions is proposed.

PHARMACEUTICAL COMPOUNDS

The invention provides compounds of the formula (1) or salts or tautomers thereof; wherein: Q is SO or SO2; n is 1 or 2; R1 is selected from hydrogen and a non-aromatic C1-6 hydrocarbon group; R2 and R3 are independently selected from hydrogen and a C1-6 hydrocarbon group; or R2 and R3 together with the carbon atom to which they are attached form a carbonyl group (C=O), a cyclopropane-1,1-diyl group or a cyclobutane-1,1-diyl group; or R together with R2 forms a C2-4 alkylene linker which is optionally substituted with one or more substituents selected from a C1-4 hydrocarbon group, halogen, hydroxy and amino; R4 and R5 are independently selected from hydrogen and a non-aromatic C1-6 hydrocarbon group; or R4 and R5 together with the carbon atom to which they are attached form a cyclopropane-1,1-diyl group or a cyclobutane-1,1-diyl group; and Ar1 is selected from phenyl, thiophenyl and furanyl,each being optionally substituted. The compounds are useful in medicine, for example in the treatment of diseases, such as cancers.

Contiguous generation of quaternary and tertiary stereocenters: One-pot synthesis of chroman-fused S-proline-derived chiral oxazepinones

A new class of chroman-fused S-proline-derived chiral oxazepinones has been synthesized in one pot through contiguous generation of quaternary and tertiary stereocenters.