(S)-(-)-1-BENZYL-2-PYRROLIDINEMETHANOL Chemical Properties

Boiling point:

115-120 °C/0.5 mmHg (lit.)

Density 

1.08 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.541(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

pka

14.77±0.10(Predicted)

form 

liquid

Appearance

Light yellow to yellow Liquid

optical activity

[α]20/D 72.7°, neat

BRN 

3663640

InChI

InChI=1S/C12H17NO/c14-10-12-7-4-8-13(12)9-11-5-2-1-3-6-11/h1-3,5-6,12,14H,4,7-10H2/t12-/m0/s1

InChIKey

ZAIQBJPTOXDDKA-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCC[C@H]1CO

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-10-34

HazardClass 

IRRITANT

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

(S)-(-)-1-BENZYL-2-PYRROLIDINEMETHANOL Usage And Synthesis

Chemical Properties

Colorless to pale yellow liquid

Uses

Precursor in the synthesis of proline-derived homochiral amine oxides. Starting material for enantiomerically pure 3-hydroxypiperidine, a structural feature present in many natural products.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of N-benzyl-L-prolinol from (R)-1-benzylpyrrolidine-2-carboxylic acid methyl ester was as follows: under nitrogen atmosphere, 25.75 g (0.68 mol) of lithium aluminum hydride (LiAlH4) was slowly added through a powder funnel into a cooled anhydrous (S)-1-benzylpyrrolidine-2-carboxylic acid methyl ester (49.6 g, 0.23 mol) tetrahydrofuran (THF, 400 mL) solution. The reaction mixture was stirred at 0 °C for 1 h and then gradually warmed up to room temperature followed by refluxing for 3 h. The reaction was carried out by stirring at 0 °C for 1 h. The reaction mixture was then refluxed for 3 h. Upon completion of the reaction, the mixture was cooled to 0 °C again to quench the reaction. The quenching process was carried out by carefully adding the cold reaction mixture to 1.5 L of ice in a 4 L conical flask fitted with a cooling bath. After the ice melted, the resulting suspension was filtered through a diatomaceous earth pad to remove the alkaline material and the solid residue was washed with 300 mL of hot ethyl acetate. The resulting biphasic filtrate was separated, the THF in the aqueous layer was removed by rotary evaporator and the residual liquid was re-extracted with an equal amount of cold ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated, and the crude product was distilled under reduced pressure (110 °C, 1.5 mmHg) to afford 41.8 g (0.22 mol) of the target product, N-benzyl-L-prolinol ((S)-5), as a colorless liquid of 97% purity.

References

[1] Heterocycles, 2012, vol. 86, # 2, p. 1275 - 1300
[2] Letters in Organic Chemistry, 2018, vol. 15, # 5, p. 352 - 358
[3] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8625 - 8632
[4] Tetrahedron, 2011, vol. 67, # 7, p. 1485 - 1500
[5] European Journal of Organic Chemistry, 2002, # 19, p. 3304 - 3314

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