BOC-HYP-OL

Base Information

• Chemical Name: BOC-HYP-OL
• CAS No.: 61478-26-0
• Molecular Formula: C10H19NO4
• Molecular Weight: 217.265
• Hs Code.: 29339900
• Mol file: 61478-26-0.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 4-hydroxy-2-(hydroxymethyl)-, 1,1-dimethylethylester, (2S-trans)-;tert-Butyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate;tert-Butyl(2S,4R)-4-hydroxy-2-hydroxymethylpyrrolidine-1-carboxylate;

Chemical Property of BOC-HYP-OL

Chemical Property:

• Melting Point: 81-86 °C(lit.)
• Refractive Index: 1.511
• Boiling Point: 340.296 °C at 760 mmHg
• PKA: 14.57±0.40(Predicted)
• Flash Point: 159.605 °C
• PSA: 70.00000
• Density: 1.19 g/cm³
• LogP: 0.28690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

(2S,4R)-4-Hydroxy-2-(hydroxymethyl)-1-pyrrolidinecarboxylicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: BOC-HYP-OL is a useful reactant used in the preparation of 4-purinylpyrrolidine nucleosides, kinase inhibitors and antibacterial agents.

Technology Process of BOC-HYP-OL

There total 2 articles about BOC-HYP-OL 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate (61478-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent

2: 95 percent / borane-dimethyl-sulfide / tetrahydrofuran / 1.) room temperature, 30 min, 2.) reflux, 2.5 h

With dimethylsulfide borane complex; In tetrahydrofuran;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate (61478-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane

2: lithium borohydride / tetrahydrofuran

With lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane;

Reference yield: 95.0%

trityl chloride (76-83-5) + tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate (61478-26-0) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → tert-butyl (2S,4R)-4-methoxy-2-((trityloxy)methyl)pyrrolidine-1-carboxylate (1315590-90-9)

Guidance literature:

With dmap; triethylamine; at 60 ℃; for 4h; Cooling with ice;

DOI:10.1016/j.bmc.2021.116514

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

di-tert-butyl dicarbonate

Downstream raw materials:

(2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine

tert-butyl (2S,4R)-4-hydroxy-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)-pyrrolidine-1-carboxylate

(2S,4S)-4-Diphenylphosphanyl-2-methoxymethyl-pyrrolidine

(2S,4R)-(N-tert-butyloxycarbonyl)-4-(Z)-propenylproline

Refernces

• 1、 -. "Substituted Imidazopyridines as HDM2 Inhibitors". . . Retrieved 2014/07/08.
• 2、 Jordis,Sauter,Siddiqi,Kuenburg,Bhattacharya. "Synthesis of (1R,4R)- and (1S,4S)-2,5-diazabicyclo[2.2.1]heptanes and their N-substituted derivatives". . p. 925 - 930. Retrieved 2007/10/02.