(R)-2-Aminomethyl-4-boc-morpholine

(R)-2-Aminomethyl-4-boc-morpholine Property

Boiling point:

311℃

Density 

1.078

Flash point:

142℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

9.37±0.29(Predicted)

Appearance

Colorless to off-white Solid-Liquid Mixture

optical activity

24.83°(C=0.01g/ml MEOH)

InChI

InChI=1S/C10H20N2O3/c1-10(2,3)15-9(13)12-4-5-14-8(6-11)7-12/h8H,4-7,11H2,1-3H3/t8-/m1/s1

InChIKey

MTMBHUYOIZWQAJ-MRVPVSSYSA-N

SMILES

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

Safety

HS Code 

2934999090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

(R)-2-Aminomethyl-4-boc-morpholine Chemical Properties,Usage,Production

Synthesis

Step 3. tert-Butyl (S)-2-(azidomethyl)morpholine-4-carboxylate (1.0 eq.) was dissolved in ethanol (0.1 M) under argon protection. To this solution was added Pd/C catalyst (0.20 eq.), followed by three evacuations of the reaction system and replacement with hydrogen gas. The reaction mixture was stirred at room temperature and under atmospheric pressure hydrogen atmosphere (using a hydrogen balloon) for 24 hours. Upon completion of the reaction, the hydrogen was removed by evacuation and the reaction system was replaced with argon. The reaction mixture was filtered through a diatomaceous earth pad and concentrated under reduced pressure to afford tert-butyl (R)-2-(aminomethyl)morpholine-4-carboxylate as a white solid in 91% yield.LCMS analysis showed (m/z) [M+H]+ = 217.1 and retention time (Rt) = 0.43 min.

References

[1] Patent: US2014/275003, 2014, A1. Location in patent: Paragraph 0188
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 15, p. 4810 - 4819
[3] Patent: US2015/259350, 2015, A1. Location in patent: Paragraph 0065; 0073
[4] Patent: KR101745741, 2017, B1. Location in patent: Paragraph 0119; 0132