N-Boc-L-cyclohexylglycinol

Base Information

• Chemical Name: N-Boc-L-cyclohexylglycinol
• CAS No.: 107202-39-1
• Molecular Formula: C13H25NO3
• Molecular Weight: 243.346
• Hs Code.: 2924299090
• Mol file: 107202-39-1.mol

Synonyms:Carbamicacid, (1-cyclohexyl-2-hydroxyethyl)-, 1,1-dimethylethyl ester, (S)-;Carbamicacid, [(1S)-1-cyclohexyl-2-hydroxyethyl]-, 1,1-dimethylethyl ester (9CI);tert-Butyl [(1S)-1-cyclohexyl-2-hydroxyethyl]carbamate;(S)-2-(tert-Butoxycarbonylamino)-2-cyclohexylethanol;Carbamic acid,N-[(1S)-1-cyclohexyl-2-hydroxyethyl]-, 1,1-dimethylethyl ester;

Chemical Property of N-Boc-L-cyclohexylglycinol

Chemical Property:

• Vapor Pressure: 5.05E-07mmHg at 25°C
• Melting Point: 83-87 ºC
• Refractive Index: 1.482
• Boiling Point: 371.2 ºC at 760 mmHg
• PKA: 12.07±0.46(Predicted)
• Flash Point: 178.3 ºC
• PSA: 58.56000
• Density: 1.037 g/cm³
• LogP: 2.84320
• Storage Temp.: Store at 0-5°C

Purity/Quality:

98%, ^*data from raw suppliers

N-Boc-L-cyclohexylglycinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Boc-L-cyclohexylglycinol

There total 11 articles about N-Boc-L-cyclohexylglycinol 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: 95.17%

N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3) + isobutyl chloroformate (543-27-1) → (S)-1-(cyclohexyl-2-hydroxyethyl)crabamic acid tert-butyl ester (107202-39-1)

Guidance literature:

N-(tert-butoxycarbonyl)-L-cyclohexylglycine; isobutyl chloroformate; With 4-methyl-morpholine; In tetrahydrofuran; at -10 - 20 ℃; for 0.5h; Inert atmosphere;

With sodium tetrahydroborate; water; In tetrahydrofuran; at -10 ℃; for 1h; Inert atmosphere;

Reference yield: 66.0%

C17H29NO6 → (S)-1-(cyclohexyl-2-hydroxyethyl)crabamic acid tert-butyl ester (107202-39-1)

Guidance literature:

With sodium tetrahydroborate; In water; at 0 ℃;

DOI:10.1016/j.bmcl.2003.09.088

Reference yield:

N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3) → (S)-1-(cyclohexyl-2-hydroxyethyl)crabamic acid tert-butyl ester (107202-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NEt₃ / tetrahydrofuran / -10 °C

2: 66 percent / NaBH₄ / H₂O / 0 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; water;

DOI:10.1016/j.bmcl.2003.09.088

upstream raw materials:

tert-butyl (S)-(methoxycarbonyl)(cyclohexyl)methylcarbamate

(2S)-amino(cyclohexyl)ethanoic acid

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

1-bromo-5-chloropentane

Downstream raw materials:

(S)-5-bromo-3-(N-tert-butoxycarbonyl-2-amino-2-cyclohexylethyl)-1-(2,6-difluorobenzyl)-6-methyluracil

C₁₅H₂₉NO₃

2-[(4S)-7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]-N-{(1S)-1-cyclohexyl-2-[4-(dimethylamino)piperidin-1-yl]ethyl}acetamide

N-[(1S)-1-cyclohexyl-2-(4-methylpiperazin-1-yl)ethyl]-2-[(4S)-7-(2-fluoropyridin-4-yl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetamide

Refernces

• 1、 Hou, Wenduan,Wei, Qi,Liu, Guisheng,Chen, Jing,Guo, Jing,Peng, Yungui. "Asymmetric Multicomponent Sulfa-Michael/Mannich Cascade Reaction: Synthetic Access to 1,2-Diamino-3-Organosulfur Compounds and 2-Nitro Allylic Amines". supporting information. p. 4870 - 4873. Retrieved 2015/10/12.
• 2、 Catalano, John G,Deaton, David N,Furfine, Eric S,Hassell, Annie M,McFadyen, Robert B,Miller, Aaron B,Miller, Larry R,Shewchuk, Lisa M,Willard Jr., Derril H,Wright, Lois L. "Exploration of the P1 SAR of aldehyde cathepsin K inhibitors.". . p. 275 - 278. Retrieved 2007/10/03.