Trimethylsilyl isocyanate → HCID 15703613, compound

HRID 2287830Notes

Reaction equation

HRID 2287830 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C@@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C([Li])(C)(C)C.C[Si]([N:28]=[C:29]=[O:30])(C)C>O1CCCC1>[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C@H:5]1[CH2:6][C:7]2[CH:8]=[C:9]([C:29]([NH2:28])=[O:30])[CH:10]=[CH:11][C:12]=2[CH2:13][CH2:14]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 70696Trimethylsilyl isocyanateHCID 54155960HCID 54155960, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 15703613HCID 15703613, compoundYield 132.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-2-(dipropylamino)-7-bromo-1,2,3,4-tetrahydronaphthalene (7) (13.02 g) in dry tetrahydrofuran was cooled to -78° C. t-Butyllithium (1.7 M in pentane, 50.6 ml) was added via syringe over a period of 6 minutes, and the mixture was stirred for an additional 8 minutes. Trimethylsilylisocyanate (13.4 ml, 85% pure, 84.1 mmol) was added in one dose, and the mixture stirred at -78° C. for 10 minutes and at room temperature for 1.5 hours. The reaction mixture was quenched with 10% hydrochloric acid, and after stirring for 30 minutes, it was basified with 15% sodium hydroxide. The free base was extracted with diethylether and 1:1 tetrahydrofuran/diethylether. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave an oil (15.25 g). Crystallization from ethyl acetate/hexane gave off-white crystals (6.30 g), m.p. 132-132° C. [α]D =+67° (25° C., CH3OH, c=0.8139).

Workup

  1. additionwas added via syringe over a period of 6 minutes
  2. stirringthe mixture stirred at -78° C. for 10 minutes and at room temperature for 1.5 hours
  3. customThe reaction mixture was quenched with 10% hydrochloric acid
  4. stirringafter stirring for 30 minutes
  5. extractionThe free base was extracted with diethylether and 1:1 tetrahydrofuran/diethylether
  6. washThe combined extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-cb06d76ea48e41cabb184e471c5bae09
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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