(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one

Product Name(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one
CAS130931-83-8
MFC6H7NO
MW109.13
EINECS627-840-6
MOL File130931-83-8.mol

Chemical Properties

Melting point	94-97 °C(lit.)
Boiling point	319.3±0.0 °C(Predicted)
Density	1.198±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
pka	15.48±0.20(Predicted)
form	powder
color	Off-white
optical activity	[α]20/D +565°, c = 1 in chloroform
InChI	InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1
InChIKey	DDUFYKNOXPZZIW-CRCLSJGQSA-N
SMILES	[C@]12([H])C[C@]([H])(C=C1)C(=O)N2
CAS DataBase Reference	130931-83-8(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
HS Code	2914290090
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

OFF-WHITE TO BEIGE CRYSTALLINE POWDER

Uses

This lactam and its antipode are precursors to the enantiomers of the carbocyclic nucleoside carbovir. It has been demonstrated that (-)-carbovir is a potent inhibitor of HIV-1 and based on clinical trials it could become an alternative to AZT. AZT is a trademark of The Wellcome Foundation Ltd.

Synthesis

2-Azabicyclo[2.2.1]hept-5-en-3-one, 2-(hydroxymethyl)-, (1S,4R)-

157810-20-3

49805-30-3

GENERAL METHOD: Unreacted N-hydroxymethyl-γ-lactams (1S,4R)-1 and (1R,4S)-2 (20 mg, 0.14 mmol) were dissolved in methanol (2 mL). Subsequently, ammonium hydroxide (2 mL) was added and the reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the solvent was removed by rotary evaporator and the residue was purified by silica gel column chromatography, using ethyl acetate as eluent, to afford white crystals of (1S,4R)-3 [15 mg, 95%; [α]D25 = +545 (c 0.3, CHCl3), ee = 99%; literature value 13: [α]D25 = +549 (c 0.26, CHCl3), ee > 99%; melting point 95-98°C (recrystallized from i-Pr2O), literature value 13: 97-100°C] or (1R,4S)-4 [15 mg, 93%; [α]D25 = +125.5 (c 0.55, CHCl3), ee = 96%; literature value 13: [α]D25 = +158 (c 0.45, CHCl3), ee > 99%; melting point 78-81°C (recrystallized from i-Pr2O), literature value 13: 78-81°C]. （1H NMR (400 MHz, CDCl3, 25 °C, TMS) data for (1S,4R)-3: δ = 2.18-2.43 (m, 2H, CH2); 3.18-3.24 (m, 1H, CHCO); 4.30-4.37 (m, 1H, CHNH); 6.05 (br s, 1H, NH); 6.63-6.82 ( m, 2H, CH=CH). Elemental analysis: calculated values (C6H7NO): C, 66.04; H, 6.47; N, 12.84; measured values: C, 66.12; H, 6.38; N, 12.82. 1H NMR (400 MHz, CDCl3, 25 °C, TMS) data for (1R,4S)-4: δ = 1.33-1.97 (m, 6H, 3 × CH2) ; 2.76-2.85 (m, 1H, CHCO); 3.04 (br s, 1H, NH); 3.95-4.08 (m, 1H, CHNH). Elemental analysis: calculated values (C6H9NO): C, 64.84; H, 8.16; N, 12.60; measured values: C, 64.81; H, 8.13; N, 12.68.

References

[1] Tetrahedron Asymmetry, 2016, vol. 27, # 16, p. 729 - 731
[2] Tetrahedron Asymmetry, 1996, vol. 7, # 8, p. 2381 - 2386
[3] Tetrahedron: Asymmetry, 1994, vol. 5, # 7, p. 1155 - 1156

(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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