tert-Butanol → HCID 67002375, compound

HRID 2191591Notes

Reaction equation

HRID 2191591 reaction equation
[CH:1]1([C:4]([C:6]2(C(O)=O)[CH2:10][CH2:9][CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.C([N:16](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:38]([O-:41])(O)=[O:39].[Na+].[CH3:43][C:44](O)([CH3:46])[CH3:45]>>[C:44]([O:41][C:38](=[O:39])[NH:16][C:6]1([C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10]1)([CH3:46])([CH3:45])[CH3:43]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 67001993HCID 67001993, compound

Product 1

HCID 67002375HCID 67002375, compoundYield 13%

Procedure

To a solution of 1-cyclopropanecarbonyl-cyclopentane carboxylic acid (0.36 g, 2.0 mmol) in t-BuOH (10 mL) was added triethylamine (0.33 mL, 2.4 mmol) followed by diphenylphosphoryl azide (0.47 mL, 2.2 mmol). The reaction mixture was stirred at reflux for 6 h then cooled to room temperature and poured into saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc (3×). The combined organics were dried over Na2SO4 and concentrated. The residue was purified by chromatography on 24 g SiO2 (0% to 30% EtOAc/hexanes) to afford 63 mg (13%) of (1-cyclopropanecarbonyl-cyclopentyl)-carbamic acid tert-butyl ester as a white solid.

Workup

  1. temperatureat reflux for 6 h
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on 24 g SiO2 (0% to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-47a5db060e2e4d6dac5963c678a7dbd7
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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