tert-Butanol → HCID 53256967, compound

HRID 1262323Notes

Reaction equation

HRID 1262323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2(C(O)=O)[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C([N:19]([CH2:23]C)C(C)C)(C)C.[C:25]([OH:29])([CH3:28])([CH3:27])[CH3:26].C1C=CC([O:36]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1>>[C:25]([O:29][C:23](=[O:36])[NH:19][C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:10][CH2:11][CH2:12]1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 123414Diphenylphosphoryl azideHCID 232950271-(3-Methoxyphenyl)cyclobutane-1-carboxylic acid

Product 1

HCID 53256967HCID 53256967, compoundYield 65%

Conditions

Temperature
110 °C

Procedure

Into a 1-neck round-bottom flask, 1-(3-Methoxy-phenyl)-cyclobutanecarboxylic acid (5.00 g, 24.2 mmol), N,N-Diisopropylethylamine (7.52 g, 58.2 mmol), tert-Butyl alcohol (100 mL, 1000 mmol) and Diphenylphosphonic azide (8.01 g, 29.1 mmol) were added. The reaction was heated at 110° C. overnight. The solvent was removed under vacuum to give a semi solid. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum to give an oil. The reaction mixture was purified via ISCO column chromatography with hexane and EtOAc. The collected fractions afforded [1-(3-Methoxy-phenyl)-cyclobutyl]-carbamic acid tert-butyl ester as a clear oil (4.20 g, 65%).

Workup

  1. customThe solvent was removed under vacuum
  2. customto give a semi solid
  3. customThe reaction was partitioned with water and DCM
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over Na2SO4
  7. filtrationThe solid was filtered
  8. washwashed with DCM
  9. customThe solvent was removed under vacuum
  10. customto give an oil
  11. customThe reaction mixture was purified via ISCO column chromatography with hexane and EtOAc

Sources & evidence

ORD record
ord-7617502775f04bcc8de580284d5f89d6
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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