Cyclobutanecarboxylic acid → 1-(Cyclopropylmethyl)cyclobutane-1-carboxylic acid

HRID 2057163Notes

Reaction equation

HRID 2057163 reaction equation
[CH:1]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.Br[CH2:9][CH:10]1[CH2:12][CH2:11]1.C1(CC2(CO)CCC2)CC1.C1(CC2(C=O)CCC2)CC1.C1(CC2(C(O)C#C)CCC2)CC1.C([Si](OC(C1(CC2CC2)CCC1)C#C)(C)C)(C)(C)C.[Si](OC(C1(CC2CC2)CCC1)C#CCO)(C(C)(C)C)(C)C>CCOC(C)=O.CCCCCC>[CH:10]1([CH2:9][C:1]2([C:5]([OH:7])=[O:6])[CH2:4][CH2:3][CH2:2]2)[CH2:12][CH2:11]1

Participants

9

Reactant 7

HCID 19494Cyclobutanecarboxylic acidHCID 81503BromomethylcyclopropaneHCID 668888844-{[Tert-butyl(dimethyl)silyl]oxy}-4-[1-(cyclopropylmethyl) cyclobutyl]but-2-yn-1-olHCID 66889412[1-(Cyclopropylmethyl)cyclobutyl]methanolHCID 858257911-(Cyclopropylmethyl)cyclobutane-1-carbaldehydeHCID 867606171-[1-(Cyclopropylmethyl)cyclobutyl]prop-2-yn-1-olHCID 86760618Tert-butyl({1-[1-(cyclopropylmethyl)cyclobutyl]prop-2-ynyl}oxy) dimethylsilane

Product 1

HCID 450847861-(Cyclopropylmethyl)cyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared according to the procedure described for Intermediate 15.1 from cyclobutanecarboxylic acid and (bromomethyl)cyclopropane. Intermediate 19.2: [1-(cyclopropylmethyl)cyclobutyl]methanol. The title compound was prepared according to the procedure described for Intermediate 15.2 from intermediate 19.1. Intermediate 19.3: 1-(cyclopropylmethyl)cyclobutanecarbaldehyde. The title compound was prepared according to the procedure described for Intermediate 15.3 from intermediate 19.2. Intermediate 19.4: 1-[1-(cyclopropylmethyl)cyclobutyl]prop-2-yn-1-ol. The title compound was prepared according to the procedure described for Intermediate 15.4 from intermediate 19.3. Intermediate 19.5: tert-butyl({1-[1-(cyclopropylmethyl)cyclobutyl]prop-2-ynyl}oxy) dimethylsilane. The title compound was prepared according to the procedure described for Intermediate 15.5 from intermediate 19.4. Rf 0.8 (EtOAc/hexanes 1/9). Intermediate 19.6: 4-{[tert-butyl(dimethyl)silyl]oxy}-4-[1-(cyclopropylmethyl) cyclobutyl]but-2-yn-1-ol.

Workup

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

Sources & evidence

ORD record
ord-cea4880982664d35bbe6a1aba5846d78
Source dataset
uspto-grants-2008_02
Patent number
US07335680B2

Reaction notes

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