Trimethylsilyl isocyanate → HCID 54145025, compound

HRID 375776Notes

Reaction equation

HRID 375776 reaction equation
Br[C:2]1[C:7]2[C@H:8]3[C@H:13]([CH2:14][CH2:15][C:6]=2[CH:5]=[CH:4][CH:3]=1)[N:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])[CH2:11][CH2:10][CH2:9]3.C[Si]([N:27]=[C:28]=[O:29])(C)C>O1CCCC1.CCCCC>[NH2:27][C:28]([C:2]1[C:7]2[C@H:8]3[C@H:13]([CH2:14][CH2:15][C:6]=2[CH:5]=[CH:4][CH:3]=1)[N:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])[CH2:11][CH2:10][CH2:9]3)=[O:29]

Participants

5

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 54402910HCID 54402910, compound

Product 1

HCID 54145025HCID 54145025, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of the (-)-trans-1,2,3,4,4a,5,6,10b-octahydro-10-bromo-4-(methylphenyl)benzo[f]quinoline (B-8, 6.60 g, 18.5 mmol) in dry tetrahydrofuran (50 mls) under nitrogen was cooled to -78° C., and t-bulyllithium (1.7M in pentane, 22.3 mls, 38.1 mmol) was added in about 10 seconds. The mixture was stirred at -78° C. for 5 minutes, and trimethylsilylisocyanate (46.5 mmol) was added via a syringe in one shot. The cold bath was removed, and the mixture was stiffed at ambient temperature for 1.5 hours. Water (30 mls) was added, and the mixture was stiffed for 10 minutes. Hydrochloiric acid (10%, 10 mls) was added, and file mixture was stiffed for 30 minutes. The mixture was bascified with 15% NaOH and extracted 3 times with methylene chloride. The extracts were dried (MgSO4), and the solvent was removed under vacuum to leave a white solid containing solvent (10.76 g). A sample (0.52 g) was crystallized from acetonitrile (20 mls) to yield the title compound (-) B-9 as white crystals (0.21 g, m.p. 189°-190° C., [α]D =-183.7° (25° C., THF, C=0.705)).

Workup

  1. customThe cold bath was removed
  2. waitthe mixture was stiffed at ambient temperature for 1.5 hours
  3. additionWater (30 mls) was added
  4. waitthe mixture was stiffed for 10 minutes
  5. additionHydrochloiric acid (10%, 10 mls) was added
  6. waitfile mixture was stiffed for 30 minutes
  7. extractionextracted 3 times with methylene chloride
  8. dry with materialThe extracts were dried (MgSO4)
  9. customthe solvent was removed under vacuum
  10. customto leave a white solid
  11. customA sample (0.52 g) was crystallized from acetonitrile (20 mls)

Sources & evidence

ORD record
ord-29b27af23dac4da9a511e51fcf2fe033
Source dataset
uspto-grants-1996_01
Patent number
US05486611

Reaction notes

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