(1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane

Base Information

• Chemical Name: (1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane
• CAS No.: 88947-07-3
• Molecular Formula: C₁₇H₃₁B
• Molecular Weight: 246.244
• Mol file: 88947-07-3.mol

Synonyms:(1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane

Chemical Property of (1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane

There total 2 articles about (1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane 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: 75.0%

1-methylcyclohex-1-ene (591-49-1) + monoisopinocampheylborane → (1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane (88947-07-3)

Guidance literature:

In diethyl ether; (N2); -35°C; 12 h; isolation of crystals; washing (Et2O, -30°C); drying; suspendingin THF; allowing to age for 12 h at 0°C; decanting; washing the solid (Et2O; 0°C); drying;

DOI:10.1021/ja00281a050

Reference yield: 75.0%

1-methylcyclohex-1-ene (591-49-1) + ((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane (64234-27-1) → (1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane (88947-07-3)

Guidance literature:

In diethyl ether; adding 1-methylcyclohexene to IpcBH2 in ether at -35°C, kept for 12 h; cryst. washed, dried, suspended in THF, aged 12 h, supernatant decanted, solid washed with ether, dried; 99% ee;;

DOI:10.1021/ja00213a028

Reference yield: 85.0%

(1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane (88947-07-3) + acetaldehyde (75-07-0,9002-91-9) + trimethyleneglycol (504-63-2) → (1'S,2'S)-(+)-2-(trans-2'-methylcyclohexyl)-1,3,2-dioxaborinane (97235-25-1)

Guidance literature:

With hydrogenchloride; sodium hydroxide; In diethyl ether; byproducts: (CH3)C7H8(CH3)2; (N2); mixing at 0°C; stirring at 25°C for 6 h; addn. of H2O and stirring for 0.5 h; evapn. of CH3CHO; addn. of C5H12; extn. with 3 M NaOH; aq. phase cooling to 0°C; acidifying; extn. (Et2O); drying; evapn.; addn. of 1,3-propanediol; distn.;

DOI:10.1021/ja00281a050

upstream raw materials:

1-methylcyclohex-1-ene

((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane

Downstream raw materials:

(E)-1-(1'S,2'S-trans-methylcyclohexyl)-2-butylethylene

(1'S,2'S)-(+)-2-(trans-2'-methylcyclohexyl)-1,3,2-dioxaborinane

(1S,2S)-diethyl trans-(2-methylcyclohexyl)boronate

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene