1-Methylcyclobutanol → (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[2-(1-methyl-cyclobutoxycarbonyl)-ethynyl]-cyclopropane-carboxylate

HRID 464465Notes

Reaction equation

HRID 464465 reaction equation
[CH3:1][C:2]1([CH3:29])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C@H:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11].[CH3:30][C:31]1(O)[CH2:34][CH2:33][CH2:32]1>>[CH3:1][C:2]1([CH3:29])[C@@H:4]([C:5]#[C:6][C:7]([O:9][C:31]2([CH3:30])[CH2:34][CH2:33][CH2:32]2)=[O:8])[C@H:3]1[C:10]([O:12][C@H:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11]

Participants

3

Reactant 2

HCID 1406421-MethylcyclobutanolHCID 13093796(S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate

Product 1

HCID 86739009(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[2-(1-methyl-cyclobutoxycarbonyl)-ethynyl]-cyclopropane-carboxylateYield 58.9%

Conditions

Temperature
20 °C

Procedure

Using the procedure of Step A of Example 15, 3.9 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate and 4.3 g of 1-methylcyclobutanol were reacted with stirring at 20° C. for 18 hours. The product was chromatographed over silica gel and was eluted with an 85-15 cyclohexane-ethyl acetate mixture to obtain 2.7 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-(1-methyl-cyclobutoxycarbonyl)-ethynyl]-cyclopropane-carboxylate melting at 76° C.

Workup

  1. customwere reacted
  2. customThe product was chromatographed over silica gel
  3. washwas eluted with an 85-15 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-f4831f8377f24e7586bbe80a005e533d
Source dataset
uspto-grants-1985_10
Patent number
US04547522

Reaction notes

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