Sodium Azide → HCID 59180171, compound

HRID 601943Notes

Reaction equation

Cl[C:2]1[CH2:7][CH:6]2[CH:4]([CH2:5]2)[C:3]=1/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11].[N-:15]=[N+]=[N-].[Na+]>>[CH2:13]([O:12][C:10]([C:9]1[NH:15][C:2]2[CH2:7][C@@H:6]3[CH2:5][C@@H:4]3[C:3]=2[CH:8]=1)=[O:11])[CH3:14]

Participants

Reactant 2

HCID 33557Sodium Azide

HCID 131728744HCID 131728744, compound

Product 1

HCID 59180171HCID 59180171, compound

Procedure

(E)-Ethyl 3-(3-chlorobicyclo[3.1.0]hex-2-en-2-yl)acrylate (142 mg, 0.67 mmol) was reacted with sodium azide (65 mg, 1.00 mmol) according to General Procedure 1.1.C. The product was purified by chromatography eluting with heptane-EtOAc, gradient 0 to 10% EtOAc to afford the title compound. 38 mg. 1H NMR (CHLOROFORM-d) δ: 8.67 (br. s., 1H), 6.71 (d, J=1.7 Hz, 1H), 4.28 (q, J=7.1 Hz, 2H), 2.95 (dd, J=16.6, 6.6 Hz, 1H), 2.73 (d, J=16.6 Hz, 1H), 1.87-2.07 (m, 2H), 1.34 (t, J=7.1 Hz, 3H), 1.02 (td, J=7.6, 4.7 Hz, 1H), 0.17 (q, J=4.2 Hz, 1H).

Workup

customThe product was purified by chromatography
washeluting with heptane-EtOAc, gradient 0 to 10% EtOAc

Sources & evidence

ORD record: ord-7304880f3879486b9e696f29c642b82e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902252B2

Reaction notes

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