(R)-5-bromo-1-cyanopentyl alcohol

Base Information

• Chemical Name: (R)-5-bromo-1-cyanopentyl alcohol
• CAS No.: 164472-77-9
• Molecular Formula: C₆H₁₀BrNO
• Molecular Weight: 192.055
• Mol file: 164472-77-9.mol

Synonyms:(R)-5-bromo-1-cyanopentyl alcohol

Chemical Property of (R)-5-bromo-1-cyanopentyl alcohol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-bromo-1-cyanopentyl alcohol

There total 1 articles about (R)-5-bromo-1-cyanopentyl alcohol 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:

(+/-)-2-methyl-2-hydroxyhexanenitrile (4111-12-0) + 5-bromopentanal (1191-30-6) → (R)-2-hydroxy-2-methylhexanenitrile (135415-89-3) + (S)-2-hydroxy-2-methylhexanenitrile + (S)-5-bromo-1-cyanopentyl alcohol + (R)-5-bromo-1-cyanopentyl alcohol (164472-77-9)

Guidance literature:

In di-isopropyl ether; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; crude extract of almond containing (R)-oxynitrilase;

DOI:10.1039/c39950000989

Reference yield:

(R)-5-bromo-1-cyanopentyl alcohol (164472-77-9) → pipecolinic acid (3105-95-1,83680-83-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2: CH₂Cl₂ / 24 h / -65 °C

3: Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

4: HCl gas / 24 h / 0 °C

5: 0.5 N aq. HCl / ethanol / 48 h / 0 °C

6: 6 N aq. HCl / 10 h / Heating

7: H₂, 3 N aq. HCl / 20percent Pd(OH)2/C / methanol / 15 h / Ambient temperature

With pyridine; hydrogenchloride; hydrogen; triethylamine; palladium dihydroxide; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0957-4166(98)00140-2

Reference yield:

(R)-5-bromo-1-cyanopentyl alcohol (164472-77-9) → (S)-2-(Benzyloxycarbonylamino-methyl)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2: CH₂Cl₂ / 24 h / -65 °C

3: Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

4: 96 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

5: 100 percent / H₂, 3 N aq. HCl / 20percent Pd(OH)2/C / methanol / 15 h / 2068.6 Torr

6: 55 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 16 h / Ambient temperature

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; hydrogen; sodium carbonate; triethylamine; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0957-4166(98)00140-2

upstream raw materials:

(+/-)-2-methyl-2-hydroxyhexanenitrile

5-bromopentanal

Downstream raw materials:

(R)-(-)-benzyl N-(6-bromo-2-hydroxyhexyl)carbamate

(R)-(-)-1-(benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxy)azepane

(R)-(-)-benzyl N-[6-bromo-2-(tert-butyldimethylsilyloxy)hexyl]carbamate

(S)-N-benzyl-2-aminomethylpiperidine