Boc-D-prolinol Chemical Properties

Melting point:

60-64 °C (lit.)

alpha 

49 º (589nm, =1.3, CHCl3)

Boiling point:

289.5±13.0 °C(Predicted)

Density 

1.084±0.06 g/cm3(Predicted)

refractive index 

54 ° (C=5, MeOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

14.77±0.10(Predicted)

form 

Crystalline Powder

color 

White to light beige

optical activity

[α]23/D +50°, c = 1.3 in chloroform

Water Solubility 

insoluble

InChI

InChI=1S/C10H19NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h8,12H,4-7H2,1-3H3/t8-/m1/s1

InChIKey

BFFLLBPMZCIGRM-MRVPVSSYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC[C@@H]1CO

CAS DataBase Reference

83435-58-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29051990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Boc-D-prolinol Usage And Synthesis

Chemical Properties

White powder

Uses

N-(tert-Butoxycarbonyl)-D-prolinol is used to prepare (azetidinyl)methoxy]pyridines and 2-(aryloxymethyl) azacyclic analogs with therapeutic potetials for the treatment of central nervous system (CNS) disorders.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Step 1: Dissolve (R)-2-(hydroxymethyl)pyrrolidine (2.0 g, 19.8 mmol) in dichloromethane (20 mL) and add 1 M aqueous sodium hydroxide solution (20 mL). A solution of di-tert-butyl dicarbonate (4.32 g, 19.8 mmol) in dichloromethane (10 mL) was added slowly and dropwise at room temperature. The reaction mixture was stirred at room temperature for 5 hours. After completion of the reaction, the organic and aqueous layers were separated. The organic layer was washed twice with distilled water and the aqueous layer was extracted with dichloromethane. All organic layers were combined and dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. Purification by recrystallization from hexane afforded the intermediate (R)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate in a yield of 2.60 g (65% yield).

References

[1] Patent: US5902819, 1999, A
[2] Patent: WO2006/19833, 2006, A1. Location in patent: Page/Page column 60
[3] European Journal of Organic Chemistry, 2002, # 14, p. 2391 - 2399
[4] Tetrahedron Letters, 1997, vol. 38, # 37, p. 6479 - 6482
[5] Tetrahedron Asymmetry, 1997, vol. 8, # 13, p. 2209 - 2213

Boc-D-prolinol(83435-58-9)Related Product Information

• Hydrogenated Cottonseed Oil
• N-Methyl-2-pyrrolidone
• Dexketoprofen trometamol
• Pyrrolidine
• Polyvinylpyrrolidone
• phytosphingosine
• Ketorolac tromethamine
• Fosfomycin tromethamine
• D(-)Prolinol
• N-Vinyl-2-pyrrolidone
• BOC-L-Prolinol
• METHYL-2-PYRROLIDONE
• 2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• BOC-L-PROLINOL LIQUID
• Boc-D-prolinol
• tert-Butoxide