(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate

(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate Property

Boiling point:

302.9±35.0 °C(Predicted)

Density 

1.026±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

11.60±0.46(Predicted)

Appearance

Colorless to off-white Solid

InChI

InChI=1S/C9H17NO3/c1-5-7(6-11)10-8(12)13-9(2,3)4/h5,7,11H,1,6H2,2-4H3,(H,10,12)/t7-/m1/s1

InChIKey

HYVYNSIWYIWTCK-SSDOTTSWSA-N

SMILES

C(OC(C)(C)C)(=O)N[C@@H](CO)C=C

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

(R)-tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of tert-butyl (R)-(1-hydroxybut-3-en-2-yl)carbamate from (R)-N-Boc-2,2-dimethyl-4-vinyl oxazolidine: vinyl oxazolidine 11 (500 mg, 2.2 mmol) was dissolved in ethanol (10 mL) under ice-bath cooling conditions, and p-toluenesulfonic acid monohydrate (42 mg, 0.22 mmol). The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the reaction was quenched with aqueous sodium bicarbonate and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, washed sequentially with saturated aqueous sodium bicarbonate (2 x 10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (eluent: hexane-ethyl acetate, v/v 9:1) to give 330 mg (80% yield) of colorless oily target compound. The 1H NMR and 13C NMR spectra of the product were in agreement with literature data [59]. Infrared spectra (ATR, cm?1) ν: 3344, 2998, 2932, 1692, 1522, 1366, 1171, 1053; 1H NMR (400 MHz, CDCl3) δ: 5.81 (m, 1H, =CH?), 5.25 (m, 2H, =CH2), 4.94 (br s, 1H, NH), 4.25 ( br s, 1H, CH?N), 3.65 (m, 2H, CH2?OH), 2.39 (br s, 1H, OH), 1.46 (s, 9H, Boc); 13C NMR (100 MHz, CDCl3) δ: 156.0, 135.4, 116.6, 79.8, 65.2, 54.7, 28.3; high-resolution mass spectra ( ESI): calculated value C9H17NO3Na [M+Na]+ m/z 210.1106, measured value 210.1109.

References

[1] Synthesis, 1994, # 12, p. 1463 - 1466
[2] Chemical Communications, 1999, # 3, p. 245 - 246
[3] Tetrahedron, 2018, vol. 74, # 38, p. 5392 - 5398
[4] Journal of Organic Chemistry, 2009, vol. 74, # 22, p. 8852 - 8855
[5] Synthesis, 1994, # 1, p. 31 - 33