(1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE Chemical Properties

Melting point:

74-76 °C(lit.)

alpha 

-44o (C=1 IN CHLOROFORM)

Boiling point:

276.4±15.0 °C(Predicted)

Density 

1.104±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Powder

pka

9.74±0.20(Predicted)

color 

White to slightly beige

optical activity

[α]22/D 44°, c = 1 in chloroform

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

6460311

InChI

InChI=1S/C10H18N2O2/c1-10(2,3)14-9(13)12-6-7-4-8(12)5-11-7/h7-8,11H,4-6H2,1-3H3/t7-,8-/m0/s1

InChIKey

UXAWXZDXVOYLII-YUMQZZPRSA-N

SMILES

[C@]12([H])C[C@]([H])(NC1)CN2C(OC(C)(C)C)=O

CAS DataBase Reference

113451-59-5(CAS DataBase Reference)

Safety Information

Risk Statements 

34

Safety Statements 

22-24/25-45-36/37/39-26

RIDADR 

3263

WGK Germany 

3

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE Usage And Synthesis

Chemical Properties

White to slightly beige powder

Uses

It is used as an active pharmaceutical intermediate.

Synthesis

Methylsulfonate 17 (1.2 g, 3.78 mmol) was used as raw material, which was suspended in anhydrous THF (38 mL), triphenylphosphine (1.48 g, 5.66 mmol) was added, and the reaction was stirred at room temperature for 2 hours. Subsequently, H2O (0.5 mL) was added and stirring was continued for 18 hours. Upon completion of the reaction, the solvent was removed under reduced pressure and the residue was suspended in 1 M hydrochloric acid (150 mL) and extracted with CH2Cl2 (2 x 70 mL). The aqueous layer was adjusted to pH 14 with base and then extracted with CH2Cl2 (3 × 70 mL). The organic phases were combined, washed with brine (100 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by rapid chromatography on silica gel with the eluent CH2Cl2-methanol-ammonia (90:9:1) afforded the target product amine 18 (0.52 g, 2.62 mmol, 71% yield) as a colorless solid. The product characterization data were as follows: melting point 76.8-77.9 °C; specific spin [α]D -47.6 (c 1.0, CHCl3); IR spectra (νmax/cm-1) 2975, 1688, 1408, 1170; 1H NMR (500 MHz, CDCl3) δ 4.43 (0.5H, s), 4.30 (0.5H, s), 3.69 (1H, s), 3.38-3.32 (1H, m), 3.19-3.13 (1H, m), 3.06-2.97 (2H, m), 1.75-1.65 (2H, m), 1.45-1.43 (9H, m); 13C NMR (125 MHz, CDCl3) δ 154.6, 154.3, 79.6, 79.5, 57.3, 56.6, 56.5, 56.3, 56.1, 52.8, 52.7, 37.2, 37.0, 28.66; mass spectra (APCI) m/z 199 ([M+H]+, 100).

References

[1] Journal of Organic Chemistry, 1988, vol. 53, # 7, p. 1580 - 1582
[2] Tetrahedron Letters, 2013, vol. 54, # 39, p. 5345 - 5347

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