(R)-3-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

289.5±13.0 °C(Predicted)

Density 

1.089

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Oil

pka

14.93±0.10(Predicted)

color 

Clear Colourless to Pale Yellow

optical activity

Consistent with structure

Water Solubility 

Slightly soluble in water

InChI

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

InChIKey

HKIGXXRMJFUUKV-MRVPVSSYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC[C@@H](CO)C1

CAS DataBase Reference

138108-72-2

Safety Information

HS Code 

2933998090

(R)-3-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Synthesis

Borane-THF complex (1.0 M, 17 mL, 16.9 mmol) was added slowly and dropwise to a stirred solution of (R)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (1.21 g, 5.6 mmol) in tetrahydrofuran (THF, 30 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature over 30 minutes, followed by heating at 45 °C for 1 hour and then at 55 °C for 90 minutes. Upon completion of the reaction, the mixture was cooled to 0 °C and quenched by careful addition of 3N hydrochloric acid (30 mL). After stirring for 20 min at room temperature, the reaction mixture was extracted with ether (Et2O, 50 mL). The organic layer was washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3, 20 mL) and brine (20 mL), dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure to afford (R)-tert-butyl-3-(hydroxymethyl)pyrrolidine-1-carboxylate (1.1 g, 91% yield) as a colorless oil.

References

[1] Patent: WO2011/150198, 2011, A1. Location in patent: Page/Page column 151
[2] Patent: WO2010/45212, 2010, A2. Location in patent: Page/Page column 299
[3] Patent: US2013/184313, 2013, A1. Location in patent: Paragraph 1541

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