(phenyl)C(Me)(iPr)(Bpin)

Base Information

• Chemical Name: (phenyl)C(Me)(iPr)(Bpin)
• CAS No.: 1257661-32-7
• Molecular Formula: C₁₇H₂₇BO₂
• Molecular Weight: 274.211
• Mol file: 1257661-32-7.mol

Synonyms:(phenyl)C(Me)(iPr)(Bpin)

Chemical Property of (phenyl)C(Me)(iPr)(Bpin)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (phenyl)C(Me)(iPr)(Bpin)

There total 3 articles about (phenyl)C(Me)(iPr)(Bpin) 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: 92.0%

2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76347-13-2) + N,N-diisopropyl carbamic acid (1-phenylethyl) ester (145167-88-0) → (phenyl)C(Me)(iPr)(Bpin) (1257661-32-7)

Guidance literature:

With sBuLi; MgBr₂; In methanol; diethyl ether; react. of C6H5CH(Me)(OCb) with sBuLi in Et2O at -78°C, iPrBpin (1.5 equiv.) added at -78°C, 1 h, MgBr2 soln. (MeOH) added at -78°C, heated to room temp., 16 h; 99% ee;

DOI:10.1002/anie.201001371

Reference yield: 62.0%

allyl bromide (106-95-6) + 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76347-13-2) + N,N-diisopropyl carbamic acid (1-phenylethyl) ester (145167-88-0) → (phenyl)C(Me)(iPr)(Bpin) (1257661-32-7) + PhC(Me)(allyl)(carbamate) (157008-79-2)

Guidance literature:

With sBuLi; In diethyl ether; react. of C6H5CH(Me)(OCb) with sBuLi at -78°C, then iPrBpin (1.2 equiv.) added, reacted for 0.5 h, BrCH2CHCH2 added, heated to room temp., 16 h; 99% ee (for PhC(Me)(iPr)(Bpin));

DOI:10.1002/anie.201001371

Reference yield: 62.0%

water-d2 (7789-20-0) + 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76347-13-2) + N,N-diisopropyl carbamic acid (1-phenylethyl) ester (145167-88-0) → (phenyl)C(Me)(iPr)(Bpin) (1257661-32-7) + PhC(Me)((2)H)(carbamate)

Guidance literature:

With sBuLi; In diethyl ether; react. of C6H5CH(Me)(OCb) with sBuLi at -78°C, then iPrBpin (1.2 equiv.) added, reacted for 0.5 h, (2)H2O added, heated to room temp., 16h; 99% ee (for PhC(Me)(iPr)(Bpin));

DOI:10.1002/anie.201001371

upstream raw materials:

allyl bromide

2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

N,N-diisopropyl carbamic acid (1-phenylethyl) ester

water-d2

Downstream raw materials:

2,3-dimethyl-1,2-diphenylbutan-1-ol

2-methyl-3-phenylbutane

Refernces

• 1、 Nagao, Kazunori,Nakamura, Kei,Ohmiya, Hirohisa,Sato, Yukiya,Yabushita, Kenya. "Tertiary alkylations of aldehydes, ketones or imines using benzylic organoboronates and a base catalyst". supporting information. p. 1065 - 1069. Retrieved 2020/11/09.