(2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine

Base Information

• Chemical Name: (2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine
• CAS No.: 135649-90-0
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• Mol file: 135649-90-0.mol

Synonyms:(2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine

Chemical Property of (2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine

There total 14 articles about (2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine 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: 87.0%

benzyl chloroformate (501-53-1,94274-21-2) + ((2S,5R)-5-Methyl-pyrrolidin-2-yl)-methanol (152231-15-7) → (2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine (135649-90-0)

Guidance literature:

With sodium hydrogencarbonate; In water; at 80 ℃; for 48h;

DOI:10.1016/0040-4039(93)88073-R

Reference yield: 75.0%

C14H18BrHgNO2 → (2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine (135649-90-0)

Guidance literature:

With sodium tetrahydroborate; oxygen; In N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)82116-3

Reference yield:

(S)-5-Hydroxymethyl-4,5-dihydro-3H-pyrrol-2-ol (17342-08-4) → (2S,5R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine (135649-90-0)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine

2: CH₂Cl₂

3: Ni(acac)2 / CHCl₃ / Heating

4: 83 percent / 5N HCl / 60 °C

5: NaHB(OAc)3 / toluene

6: 87 percent / NaHCO₃ / H₂O / 48 h / 80 °C

With pyridine; hydrogenchloride; bis(acetylacetonate)nickel(II); sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; In dichloromethane; chloroform; water; toluene;

DOI:10.1016/0040-4039(93)88073-R

upstream raw materials:

((R)-1-Methyl-pent-4-enyl)-carbamic acid benzyl ester

benzyl chloroformate

((2S,5R)-5-Methyl-pyrrolidin-2-yl)-methanol

tert-butyl (1S)-1-[(1-ethoxyethoxy)methyl]-4-oxopentylcarbamate

Downstream raw materials:

(E)-(2S,5R)-1-(benzyloxycarbonyl)-2-(11-(benzyloxy)-3-oxo-1-undecenyl)-5-methylpyrrolidine

(Z)-(2S,5R)-1-(benzyloxycarbonyl)-2-(11-(benzyloxy)-3-oxo-1-undecenyl)-5-methylpyrrolidine

(E)-(2R,5S)-1-(benzyloxycarbonyl)-2-methyl-5-(3-oxo-1-decenyl)pyrrolidine

(Z)-(2R,5S)-1-(benzyloxycarbonyl)-2-methyl-5-(3-oxo-1-decenyl)pyrrolidine