(S)-TERT-LEUCINOL Chemical Properties

Melting point:

30-34 °C(lit.)

Boiling point:

114-116 °C (10 mmHg)

Density 

0.9 g/mL at 25 °C(lit.)

refractive index 

38 ° (C=1.5, EtOH)

Flash point:

194 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Methanol

pka

12.88±0.10(Predicted)

form 

Crystalline Low Melting Mass or Liquid

color 

White or colorless

optical activity

[α]26/D +37°, c = 1.5 in ethanol

BRN 

3600321

InChI

InChI=1S/C6H15NO/c1-6(2,3)5(7)4-8/h5,8H,4,7H2,1-3H3/t5-/m1/s1

InChIKey

JBULSURVMXPBNA-RXMQYKEDSA-N

SMILES

C(O)[C@@H](N)C(C)(C)C

CAS DataBase Reference

112245-13-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-23

HS Code 

29221990

MSDS

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

(S)-TERT-LEUCINOL Usage And Synthesis

Chemical Properties

white crystalline low melting mass or

Uses

Useful amino acid employed in various asymmetric reactions.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

GENERAL STEPS: Example 8-1; To a 100 mL Schlenk tube purged with nitrogen was added 4.00 g (30.5 mmol) of (S)-tert-leucine and 40 mL of tetrahydrofuran, and the temperature of the reaction system was adjusted to 10°C. Over 5 min, 1.46 g (61.0 mmol) of lithium borohydride was added to the suspension in batches, followed by adjusting the temperature of the system to 20 °C. Over 30 minutes, 7.44 g (67.1 mmol) of trimethylmethylsilyl chloride was added slowly and dropwise, then the mixture was heated to 65 °C and stirred continuously at this temperature for 3 hours. Upon completion of the reaction, the mixture was cooled to 10 °C and quenched by the slow dropwise addition of 4 mL of methanol over 20 min. After concentrating the reaction mixture using a rotary evaporator, 40 mL of 4 M aqueous sodium hydroxide solution was added and stirred for 1 hour at room temperature. Subsequently, 40 mL of tert-butyl methyl ether was added for extraction and the organic layer was separated and dried with anhydrous sodium sulfate. After filtration to remove the desiccant, the tert-butyl methyl ether was removed by atmospheric pressure distillation. Finally, the 70 to 75 °C fraction was collected by reduced pressure distillation (0.3 kPa) to give 2.96 g of (S)-tert-leucinol in 83% yield.

References

[1] Journal of the American Chemical Society, 2003, vol. 125, # 21, p. 6362 - 6363
[2] Chemical Communications, 2010, vol. 46, # 3, p. 445 - 447
[3] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1637 - 1642
[4] Journal of Organic Chemistry, 1992, vol. 57, # 17, p. 4732 - 4740
[5] Organic Letters, 2018, vol. 20, # 16, p. 4806 - 4810

(S)-TERT-LEUCINOL(112245-13-3)Related Product Information

• (R)-(-)-TERT-LEUCINOL,(R)-TERT-LEUCINOL
• L-Serine
• (S)-(+)-2-Amino-3-methyl-1-butanol
• L-tert-Leucine
• (3R)-(-)-1-BENZYL-3-(ETHYLAMINO)PYRROLIDINE
• 1-Benzyl-3-aminopyrrolidine
• 1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE
• (S)-TERT-LEUCINOL
• 1-BENZYL-3-ACETAMIDOPYRROLIDINE
• (3S)-(+)-1-BENZYL-3-(ETHYLAMINO)PYRROLIDINE
• NEMONAPRIDE
• (3R)-(-)-1-BENZYL-3-(METHYLAMINO)PYRROLIDINE
• (S)-(+)-1-Benzyl-3-aminopyrrolidine
• 1-BENZYL-3-(ETHYLAMINO)PYRROLIDINE
• (S)-N-BOC-TERT-LEUCINOL 98,)-N-Boc-tert-leucinol
• 3,3-DIMETHYL-1-BUTANOL
• (R)-3,3-DIMETHYL-2-AMINOBUTANE
• (S)-(+)-2-Amino-1-butanol