Benzylamine → (-)-1-Methoxy-4-(1-propylallyloxy)benzene

HRID 14435Notes

Reaction equation

HRID 14435 reaction equation
C(N)C1C=CC=CC=1.C(=O)(OCC=CC1C=CC=CC=1)OC.CC1C=CC(C2C(=O)C3C(CC(O)C(O)C3)OC=2)=CC=1.CC1(C)C(C=[CH:54][C:55]2CCC/[C:57](=[CH:58]/[CH:59]=C3/C(C)(C)C4C(N/3CCCCS(O)(=O)=O)=CC=CC=4)/[C:56]=2[O:82][C:83]2[CH:88]=[CH:87][C:86]([O:89][CH2:90]CCCNCC3OC(O)C(N)C(O)C3O)=[CH:85][CH:84]=2)=[N+](CCCCS([O-])(=O)=O)C2C1=CC=CC=2>>[CH3:90][O:89][C:86]1[CH:87]=[CH:88][C:83]([O:82][CH:56]([CH2:57][CH2:58][CH3:59])[CH:55]=[CH2:54])=[CH:84][CH:85]=1

Participants

5

Reactant 4

HCID 7504Benzylamine2×HCID 54135828Methyl 3-phenylprop-2-en-1-yl carbonate2×HCID 73771032HCID 73771032, compound2×HCID 178424610HCID 178424610, compound

Product 1

HCID 15497765(-)-1-Methoxy-4-(1-propylallyloxy)benzene

Procedure

Reaction of benzylamine with methyl cinnamyl carbonate catalyzed by Complex Ir-3 and [(COE)2IrCl]2 (FIG. 2, triangles): By the procedure for reaction of the combination of Ir-2 and [(COD)IrCl]2, the reaction of benzylamine (135 mg, 1.26 mmol) and methyl cinnamyl carbonate (192 mg, 1.00 mmol) catalyzed by [(COD)Ir(κ2-L1)(PPh3)] (Ir-3) (11.0 mg, 0.0100 mmol) and [(COE)2IrCl]2 (4.4 mg, 0.0050 mmol) was monitored by GC for 10 h. 1H NMR analysis of the crude reaction showed the ratios of products to be 98/1/1, and after purification of the product by the general procedure, HPLC analysis as described above indicated that the enantiomeric excess of the major product was 97.2%.

Workup

  1. custom1H NMR analysis of the crude reaction
  2. customafter purification of the product by the general procedure, HPLC analysis

Sources & evidence

ORD record
ord-3c1e2cbd405d46fa860ec9adea1bd22e
Source dataset
uspto-grants-2010_06
Patent number
US07732365B2

Reaction notes

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