N-BOC-(METHYLAMINO)ACETALDEHYDE Chemical Properties

Boiling point:

218.2±19.0 °C(Predicted)

Density 

1.026g/ml

refractive index 

1.44

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

clear liquid

pka

-1.63±0.70(Predicted)

color 

Colorless to Light yellow

Water Solubility 

Slightly miscible with water.

Sensitive 

Air Sensitive

InChI

InChI=1S/C8H15NO3/c1-8(2,3)12-7(11)9(4)5-6-10/h6H,5H2,1-4H3

InChIKey

MSWTVSDFEYSRMQ-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)N(C)CC=O

Safety Information

HS Code 

2924297099

N-BOC-(METHYLAMINO)ACETALDEHYDE Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

N-Boc-(methylamino)acetaldehyde is involved in the preparation of benzo[d]imidazole inhibitor of co-activator associated arginine methyltransferase.

Synthesis

General procedure for the synthesis of N-Boc-(methylamino)acetaldehyde from N-BOC-N-methylaminoethanol: (a) Dess-Martin periodontane (22 g, 52 mmol) was added batchwise to a solution of 2-(N-Boc-methylamino)ethanol (8.8 g, 50 mmol) dissolved in dichloromethane at 0 °C. The reaction mixture was naturally warmed to room temperature and stirred continuously for 3 hours. Upon completion of the reaction, saturated aqueous sodium bicarbonate solution and sodium thiosulfate solution were added and stirring was continued for 0.5 hours. Subsequently, the organic phase was separated, washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated to give 9 g (quantitative yield) of the title compound N-Boc-(methylamino)acetaldehyde. The product was analyzed by GC-MS and showed m/z 174 (M + 1).

References

[1] Patent: WO2007/120098, 2007, A1. Location in patent: Page/Page column 88
[2] Patent: WO2013/68552, 2013, A1. Location in patent: Page/Page column 53
[3] ChemMedChem, 2015, vol. 10, # 3, p. 470 - 489
[4] Patent: WO2011/133039, 2011, A2. Location in patent: Page/Page column 202
[5] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 21, p. 3219 - 3225

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