Triphenylphosphine → HCID 10220866, compound

HRID 1708233Notes

Reaction equation

HRID 1708233 reaction equation
[N:1]([C:4]1[C:5](=[O:20])[CH2:6][CH2:7][C@@:8]2([CH3:19])[C:17]=1[CH2:16][CH2:15][C:14]1[C:9]2=[CH:10][CH:11]=[C:12]([Cl:18])[CH:13]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[NH2:1][C:4]1[C:5](=[O:20])[CH2:6][CH2:7][C@@:8]2([CH3:19])[C:17]=1[CH2:16][CH2:15][C:14]1[C:9]2=[CH:10][CH:11]=[C:12]([Cl:18])[CH:13]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 15230382HCID 15230382, compound

Product 1

HCID 10220866HCID 10220866, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R) -1-azido-7-chloro-4,4a, 9,10-tetrahydro-4a-methyl-2 (3H) -phenanthreneone (0.210 g, 0.730 mmol) in tetrahydrofuran (8 mL) and water (1 mL) was added triphenylphosphine (0.325 g, 1.24 mmol). After refluxing for 20 minutes the mixture was cooled and the tetrahydrofuran evaporated. The resulting system was diluted with toluene (8 mL) and refluxed for 16 hours. The mixture was evaporated and the residue was purified by chromatography (Chromatotron, Harrison Research, Palo Alto, Calif.) (15% ethyl acetate/hexane) twice to give 42 mg (22%) of the title amine as a white powder. IR (KBr) 1648 (CO)cm-1 ; 1H NMR (300 MHz, CDCl3) δ7.23 (s, 2H), 7.15 (s, 1H), 2.98-3.07 (m, 1H), 2.75-2.93 (m, 3H), 2.48-2.67 (m, 2H), 2.36-2.47 (m, 1H), 2.05-2.16 (m, 1H), 1.49 (s,3H); MS (FD)m/z 261 (M+); UV λmaxEtOH (nm) (ε) 203 (20595), 294 (6036).

Workup

  1. temperatureAfter refluxing for 20 minutes the mixture
  2. temperaturewas cooled
  3. customthe tetrahydrofuran evaporated
  4. additionThe resulting system was diluted with toluene (8 mL)
  5. temperaturerefluxed for 16 hours
  6. customThe mixture was evaporated
  7. customthe residue was purified by chromatography (Chromatotron, Harrison Research, Palo Alto, Calif.) (15% ethyl acetate/hexane) twice

Sources & evidence

ORD record
ord-995c36ba83464a888228651f8d496734
Source dataset
uspto-grants-1994_10
Patent number
US05356935

Reaction notes

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