(3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid Chemical Properties

Melting point:

140-145°C

Boiling point:

337.2±35.0 °C(Predicted)

Density 

1.201±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.47±0.20(Predicted)

form 

solid

Appearance

White to off-white Solid

optical activity

[α]/D +15.0°, c = 0.5% in chloroform

Water Solubility 

Soluble in water (slightly).

InChI

InChI=1S/C10H17NO4/c1-10(2,3)15-9(14)11-5-4-7(6-11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)/t7-/m0/s1

InChIKey

HRMRQBJUFWFQLX-ZETCQYMHSA-N

SMILES

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

CAS DataBase Reference

140148-70-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

41-50

Safety Statements 

26-39-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HS Code 

29333990

(3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

N-Boc-L-beta-proline is an important raw material and intermediate used in pharmaceuticals, agrochemicals and dyestuff.

Synthesis

General procedure for the synthesis of (R)-1-Boc-3-carboxypyrrolidine from methyl 1-Boc-pyrrolidine-3-carboxylate: sodium hydroxide (0.80 g, 20.00 mmol) was dissolved in water (15 mL), and this solution was added to a methanol (30 mL) solution of methyl 1-Boc-pyrrolidine-3-carboxylate (2.30 g, 10.00 mmol). . The reaction mixture was allowed to react for 3 hours with stirring at room temperature. After the reaction was completed, the methanol was removed by concentration under reduced pressure. The pH of the remaining aqueous solution was adjusted to 4 with 2 M glacial acetic acid and then extracted with dichloromethane (50 mL x 3). The organic phases were combined and dried with anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to give 1.80 g of an oily product in 83.00% yield.

References

[1] Organic Letters, 2005, vol. 7, # 15, p. 3287 - 3289
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 1, p. 94 - 104
[3] European Journal of Organic Chemistry, 2005, # 4, p. 673 - 682
[4] Patent: CN106336413, 2017, A. Location in patent: Paragraph 0453; 0454; 0455
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 7, p. 2052 - 2059

(3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid(140148-70-5)Related Product Information

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