149682-82-6

Basic information

• Product Name: (S)-tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate
• Synonyms: (S)-1-BOC-pyrrolidine-2-boronic acid, pinacol ester;(S)-tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate;1-Boc-pyrrolidine-2-boronic acid pinacol ester
• CAS NO: 149682-82-6
• Molecular Formula: C₁₅H₂₈BNO₄
• Molecular Weight: 297.19812
• Mol File: 149682-82-6.mol

Chemical Properties

• Melting Point: 107 °C (decomp)
• Boiling Point: 341.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.04±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: -0.86±0.40(Predicted)
• CAS DataBase Reference: (S)-tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate(149682-82-6)
• EPA Substance Registry System: (S)-tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate(149682-82-6)

Safety Data

• Hazardous Substances Data: 149682-82-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate is used as a synthetic intermediate for the development of new pharmaceuticals. Its unique structure allows for the creation of a wide range of biologically active compounds, making it a versatile building block in the synthesis of various drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate is used as a key intermediate for the preparation of complex organic molecules. Its reactivity and functional groups enable chemists to construct a diverse array of target molecules, including those with potential applications in various industries such as pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
(S)-tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate is also utilized in research and development laboratories for the exploration of new synthetic routes and methodologies. Its unique properties and reactivity make it an attractive candidate for the development of novel chemical reactions and the synthesis of innovative molecular structures.

Upstream product

• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 

Relevant articles and documents

Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds

The stereospecific cross-coupling of secondary boronic esters with sp2 electrophiles (Suzuki-Miyaura reaction) is a long-standing problem in synthesis, but progress has been achieved in specific cases using palladium catalysis. However, related couplings with tertiary boronic esters are not currently achievable. To address this general problem, we have focused on an alternative method exploiting the reactivity of a boronate complex formed between an aryl lithium and a boronic ester. We reasoned that subsequent addition of an oxidant or an electrophile would remove an electron from the aromatic ring or react in a Friedel-Crafts-type manner, respectively, generating a cationic species, which would trigger 1,2-migration of the boron substituent, creating the new C-C bond. Elimination (preceded by further oxidation in the former case) would result in rearomatization giving the coupled product stereospecifically. Initial work was examined with 2-furyllithium. Although the oxidants tested were unsuccessful, electrophiles, particularly NBS, enabled the coupling reaction to occur in good yield with a broad range of secondary and tertiary boronic esters, bearing different steric demands and functional groups (esters, azides, nitriles, alcohols, and ethers). The reaction also worked well with other electron-rich heteroaromatics and 6-membered ring aromatics provided they had donor groups in the meta position. Conditions were also found under which the B(pin)- moiety could be retained in the product, ortho to the boron substituent. This protocol, which created a new C(sp2)-C(sp3) and an adjacent C-B bond, was again applicable to a range of secondary and tertiary boronic esters. In all cases, the coupling reaction occurred with complete stereospecificity. Computational studies verified the competing processes involved and were in close agreement with the experimental observations.

A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties

(Chemical Equation Presented) A two-step, direct asymmetric synthesis of the trifluoroacetate ammonium salt of boroproline is reported. (-)-Sparteine-mediated lithiation of N-Boc-pyrrolidine afforded N-Boc-aminoboronic acid in good yield and enantioselectivity as determined by HPLC (pinanediol ester). Deprotection using TFA yielded the ammonium salt; full characterization data are presented, and the structure in aqueous solution and the occurrence of a B-N species are discussed.