HCID 18782847, compound → 2-Isopropyl-3-isothiocyanatomethyl-6,6-dimethyl-bicyclo[3.1.1]heptane
Reaction equation
[CH: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])[CH3:2].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]>>[CH: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])[CH3:2]Participants
Procedure
The same procedure that was used in example 1 was followed except that 2-isopropyl-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-Isopropyl-3-isothiocyanatomethyl-6,6-dimethyl-bicyclo[3.1.1]heptane was prepared by reduction of 2-isopropyl-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carbonitrile to the requisite amine following the procedure in step C of example 42 and subsequent conversion to the isothiocyanate using step A of example 15: C.I. m/z 588 [M+1]; 1H NMR (CDCl3)δ 10.45 (br s, 1H), 8.42-8.46 (m, 4H), 7.82 (d, J=8.1 Hz, 2H), 7.69 (d, J=8.1 Hz, 2H), 7.13 (m, 2H), 7.07 (m, 2H), 5.22 (s, 1H), 3.32 (dd, J=11.2, 13.9 Hz, 1H), 3.24 (d, J=13.1 Hz, 2H), 3.01-3.10 (m, 2H), 2.92 (dd, J=3.1, 13.9 Hz, 1H), 1.96 (m, 1H), 1.76 (m, 1H), 1.59-1.70 (m, 3H), 1.32 (m, 1H), 1.24 (m, 1H), 1.14 (s, 3H), 1.05 (d, 10.2 Hz, 1H), 0.86 (d, J=6.6 Hz, 3H), 0.78 (d, J=6.9 Hz, 3H), 0.70 (s, 3H), 0.50 (m, 1H).
Sources & evidence
- ORD record
- ord-4c1a305e6f6348d7866a504e6f671d67
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06071935
Reaction notes
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