Ethanol → HCID 58691178, compound

HRID 1392100Notes

Reaction equation

HRID 1392100 reaction equation
C(=O)(O[CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)OC.C1([C@@H]([N:23]([C@H:47]([C:49]2[CH:54]=[CH:53][CH:52]=CC=2)C)P2OC3C=CC4C=CC=CC=4C=3C3C4C(C=CC=3O2)=CC=CC=4)C)C=CC=CC=1.CCO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir]>[C:8]1([C@@H:7]([NH:23][CH:47]2[CH2:49][CH2:54][CH2:53][CH2:52]2)[CH:6]=[CH2:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 10035469HCID 10035469, compoundHCID 11731247N,N-Bis((S)-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine

Product 1

HCID 58691178HCID 58691178, compound

Reagents, catalysts & solvents 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Methyl (2E)-3-phenylprop-2-en-1-yl carbonate (384 mg) in THF (5 ml), was added N,N-bis[(1S)-1-phenylethyl]dinaphtho[1,2-f:2′,1′-d][1,3,2]dioxaphosphepin-4-amine (108 mg), and chloro(1,5-cyclooctadiene)iridium(I) dimer (27 mg) at RT under N2. The mixture was heated at reflux overnight. Evaporated material then redissoled in a 50:50 mixture of EtOH:THF. To this solution was added macro porous p-toluenesulfonic acid resin (6 g) and the mixture was gently agitated for 3 h. At this time the resin was washed completely with THF, THF:EtOH and EtOH. To a suspension of the resin in MeOH (75 ml) was added 7 N NH3.MeOH (75 ml). This mixture was gently agitated for 2 hours and filered, washing with MeOH, THF, THF:MeOH, and DCM. Evaporating this filtrate left the title compound as a yellow oil (360 mg, 89%). 1H NMR (300 MHz, CDCl3) δ 1.25-1.87 (m, 9H), 2.98-3.07 (m, 1H), 4.24 (d, 1H, J=7 Hz), 5.06-5.21 (m, 2H), 5.87-5.99 (m, 1H), 7.20-7.34 (m, 5H). MS APCI, m/z=202 (M+1), LC/MS, 1.35 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. washAt this time the resin was washed completely with THF, THF
  4. additionTo a suspension of the resin in MeOH (75 ml)
  5. additionwas added 7 N NH3
  6. stirringThis mixture was gently agitated for 2 hours
  7. washwashing with MeOH, THF, THF
  8. customEvaporating this filtrate
  9. waitleft the title compound as a yellow oil (360 mg, 89%)
  10. customMS APCI, m/z=202 (M+1), LC/MS, 1.35 min.

Sources & evidence

ORD record
ord-7aa0862aba73426ab6768473e3aec456
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

Loading…