Bis(trimethylsilyl)carbodiimide → N-(6-bromo-3'-isopropylspiro[chroman-2,1'-cyclopentane]-4-ylidene)cyanamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:16](=[CH:17][CH:18]=1)[O:15][C:7]1([CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[CH2:8]1)[CH2:6][C:5]2=O.[C:20](=[N:26][Si](C)(C)C)=[N:21][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:16](=[CH:17][CH:18]=1)[O:15][C:7]1([CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[CH2:8]1)[CH2:6][C:5]2=[N:26][C:20]#[N:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 6-bromo-3′-isopropylspiro[chroman-2,1′-cyclopentan]-4-one (250 mg, 0.776 mmol) in DCM (10 mL) was added TiCl4 (1.55 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.38 mL, 1.707 mmol) was added dropwise. The mixture was stirred at room temperature overnight and poured into ice-water (25 g). The aqueous layer was extracted with CH2Cl2, which was combined with the organic layer. The organic layer was dried and concentrated to give crude N-(6-bromo-3′-isopropylspiro[chroman-2,1′-cyclopentane]-4-ylidene)cyanamide (250 mg, 93%). 1H-NMR (CDCl3): 0.82 (m, 6H), 1.36 (m, 2H), 1.69 (m, 3H), 1.96 (m, 3H), 3.10 (d, 2H), 6.75 (m, 1H), 7.52 (m, 1H), 8.04 (d, 1H).
Workup
- stirringThe mixture was stirred at room temperature overnight
- extractionThe aqueous layer was extracted with CH2Cl2, which
- customThe organic layer was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-178005d70cdb4489b5bb3e4843cca962
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450308B2
Reaction notes
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