(S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE Chemical Properties

Boiling point:

101-102 °C2 mm Hg(lit.)

Density 

1.082 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.443(lit.)

Flash point:

199 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

pka

-3.58±0.60(Predicted)

color 

Clear yellow

optical activity

[α]20/D 55°, c = 1.3 in chloroform

CAS DataBase Reference

108149-60-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HS Code 

29349990

MSDS

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

(S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE Usage And Synthesis

Chemical Properties

Clear yellow liquid

Uses

(S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine is a useful intermediate used in the improved synthesis of Garner′s aldehyde and analogs with multiple pharmaceutical applications.

Synthesis

To a solution of Boc-L-serine methyl ester (2a, 1.94 g, 8.85 mmol, 1.00 eq.) in dichloromethane (20.0 mL) was added 2,2-dimethoxypropane (3.25 mL, 26.6 mmol, 3.00 eq.) and boron trifluoride-ether complex (0.0553 mL, 0.443 mmol, 0.500 equivalent) in a dilute solution in dichloromethane (15.0 mL). The reaction mixture was stirred at 25 °C for 3 h and then quenched with saturated aqueous NaHCO3 solution. The aqueous layer was extracted with two portions of ethyl acetate. The combined organic layers were washed with 10% NaCl aqueous solution, dried with Na2SO4, filtered, and concentrated in vacuum. Purification of the residue by silica gel column chromatography (16% hexane solution of ethyl acetate) afforded (R)-(-)-3-BOC-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine (2.28 g, 8.79 mmol, 99%) as a colorless oil.

References

[1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 106 - 110
[2] Tetrahedron Letters, 1999, vol. 40, # 1, p. 113 - 116
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 6, p. 1045 - 1051
[4] Patent: WO2015/156601, 2015, A1. Location in patent: Page/Page column 23; 24; 25
[5] Organic Letters, 2003, vol. 5, # 23, p. 4253 - 4256

(S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE(108149-60-6)Related Product Information

• BOC-N-ME-SER-OH
• ethyl (hydroxymethyl)-carbamate
• 4-OXAZOLIDINECARBOXYLIC ACID
• Boc-L-serine methyl ester
• 3-(1,1-DIMETHYLETHYL)-4-METHYL-(R,S)-2,2-DIMETHYL-3,4-OXAZOLIDINEDICARBOXYLATE
• BOC-SER(ME)-OH
• (S)-N-BOC-2-AMINO-3-ETHOXY-PROPIONIC ACID
• (S)-(-)-3-TERT-BUTOXYCARBONYL-4-FORMYL-2,2-DIMETHYL-1,3-OXAZOLIDINE
• 1,1-DIMETHYLETHYL-(R,S)-4-FORMYL-2,2-DIMETHYL-3-OXAZOLIDINECARBOXYLATE
• 3-OXAZOLIDINECARBOXYLIC ACID
• N-BOC-N-ISOPROPYL-AMINO-ACETIC ACID
• (R)-4-HYDROXYMETHYL-2,2-DIMETHYL-OXAZOLIDINE-3-CARBOXYLIC ACID TERT-BUTYL ESTER
• (S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE
• (S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID