HCID 18782830, compound → HCID 18782827, compound
Reaction equation
[C:1]([CH:4]1[CH:9]([C:10]#[N:11])[CH2:8][CH:7]2[CH2:12][CH:5]1[C:6]2([CH3:14])[CH3:13])([CH3:3])=[CH2:2].C(C1C(CN2C(=O)C(CC3C=CN=CC=3)(CC3C=CN=CC=3)NC2=CC(C2C=CC(C#N)=CC=2)=O)CC2CC1C2(C)C)(C)=C.[N-]=[C:60]=[S:61]>>[C:1]([CH:4]1[CH:9]([CH2:10][N:11]=[C:60]=[S:61])[CH2:8][CH:7]2[CH2:12][CH:5]1[C:6]2([CH3:14])[CH3:13])([CH3:3])=[CH2:2]Participants
Procedure
The same procedure that was used in example 1 was followed except that 2-isopropenyl-3-isothiocyanatomethyl-6,6-dimethyl-bicyclo[3.1.1]heptane was used in the place of (+)-3-pinanemethyl isothiocyanate in step D to give the titled compound as a tan solid. 2-Isopropenyl-3-isothiocyanatomethyl-6,6-dimethyl-bicyclo[3.1.1]heptane was prepared by reducing 2-isopropenyl-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carbonitrile to the requisite amine following the procedure in step C of example 42 and subsequently converted to the isothiocyanate using step A of example 15: C.I. m/z 586 [M+1]; 1H NMR (CDCl3)δ 10.47 (br s, 1H), 8.43-8.49 (m, 4H), 7.82 (d, J=8.7 Hz, 2H), 7.69 (d, J=8.7 Hz, 2H), 7.13 (m, 2H), 7.08 (m, 2H), 5.27 (s, 1H), 4.74 (m, 2H), 3.33 (dd, J=11.2, 13.9 Hz, 1H), 3.23 (d, J=13.5 Hz, 2H), 3.03-3.15 (m, 2H), 2.84 (dd, J=3.2, 13.9 Hz, 1H), 1.99-2.15 (m, 2H), 1.70 (m, 3H), 1.63 (s, 3H), 1.20 (m, 2H), 1.15 (s, 3H), 0.77(s, 3H), 0.66 (m, 1H).
Sources & evidence
- ORD record
- ord-43e7af4211e5435d9144566544c42c6d
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06071935
Reaction notes
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