1-Phenylcyclopropanecarboxylic acid → N-Methoxy-N-methyl-1-phenylcyclopropanecarboxamide

HRID 556887Notes

Reaction equation

HRID 556887 reaction equation
[C:1]1([C:7]2([C:10]([OH:12])=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2([C:22](=[O:25])C=C)CC2)C=CC=CC=1.COC1(OC)CC[N:30](CCC(=O)C2(C3C=CC=CC=3)CC2)[C@H:29]1C/C=C\CCCC(OC)=O.COC1(OC)CCN[C@H]1C/C=C\CCCC(OC)=O.OC(C1(C2C=CC=CC=2)CC1)CCN1CCC(OC)(OC)C1C/C=C\CCCC(OC)=O>CCOC(C)=O.CCCCCC>[CH3:22][O:25][N:30]([CH3:29])[C:10]([C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][CH2:8]1)=[O:12]

Participants

7

Reactant 5

HCID 802061-Phenylcyclopropanecarboxylic acidHCID 59659380HCID 59659380, compound2×HCID 65573956HCID 65573956, compoundHCID 66993355HCID 66993355, compoundHCID 66993392HCID 66993392, compound

Product 1

HCID 55027773N-Methoxy-N-methyl-1-phenylcyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent4×

Procedure

The title compound was prepared according to the procedure described for intermediate 16.1 from 1-phenyl-1cyclopropane carboxylic acid. Rf 0.30 (EtOAc/hexanes 3/7). Intermediate 18.2: 1-(1-phenylcyclopropyl)prop-2-en-1-one. The title compound was prepared according to the procedure described for intermediate 16.2 using intermediate 16.1. Rf 0.90 (EtOAc/hexanes 3/7). Intermediate 18.3: methyl(5Z)-7-{(2S)-3,3-dimethoxy-1-[3-oxo-3-(1-phenylcyclopropyl)propyl]pyrrolidin-2-yl}hept-5-enoate. The title compound was prepared according to the procedure described for intermediate 13.1 from methyl(5Z)-7-[(2S)-3,3-dimethoxypyrrolidin-2-yl]hept-5-enoate (intermediate 5.3) and intermediate 18.2. Rf 0.30 (EtOAc/hexanes 1/1); MS (m/z) 444 (M+1). Intermediate 18.4: methyl(5Z)-7-{1-[3-hydroxy-3-(1-phenylcyclopropyl)propyl]-3,3-dimethoxypyrrolidin-2-yl}hept-5-enoate. The title compound was prepared according to the procedure described for intermediate 13.2 from intermediate 18.3. (mixture of diastereoisomers) Rf 0.50 & 0.45 (EtOAc/hexanes 1/1); MS (m/z) 446 (M+1).

Workup

  1. customThe title compound was prepared
  2. customThe title compound was prepared
  3. customThe title compound was prepared

Sources & evidence

ORD record
ord-dc8cef1d0244470d9d5b68d19b8765f7
Source dataset
uspto-grants-2011_11
Patent number
US08058305B2

Reaction notes

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