Cesium carbonate → HCID 86629211, compound

HRID 2384934Notes

Reaction equation

HRID 2384934 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23]C2[CH:20]([O:21]2)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[C:24](=O)([O-])[O-].[Cs+].[Cs+]>C(O)C.C1OCCOCCOCCOCCOCCOC1>[C:11]([O:15][C:16]([N:18]1[CH2:19][C@@H:20]([OH:21])[C@H:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[O:10][CH3:24])[CH2:23]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1422285-Bromo-2-methoxyphenolHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 86629211HCID 86629211, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 702EthanolSolvent

Procedure

Suspend 4-bromoguaiacol (1.19 g, 5.72 mmol) and 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (prepared according to Syn. Comm. V26, Is8, p 1499, 1996) (530 mg, 2.86 mmol) in ethanol (6 mL) and add cesium carbonate (2.33 g, 7.15 mmol) and 18-crown-6 (5 mg). Heat the reaction mixture at reflux temperature for four days. Filter the mixture and evaporate the filtrate. Purify by silica gel chromatography, eluting with 0-65% EtOAc in hexanes to give 760 mg (69%) of the title compound as a yellow solid. 1H NMR (DMSO-d6): δ 7.13 (d, J=2.3 Hz, 1H), 7.04 (dd, J=8.8, 2.3 Hz, 1H), 6.97 (d, J=8.8 Hz, 1H), 5.42 (bs, 1H), 4.54 (m, 1H), 4.10 (m, 1H), 3.74 (s, 3H), 3.54 (td, J=12.6, 4.1, 1H), 3.40 (td, J=12.6, 4.1, 1H), 3.31 (m, 1H), 3.22 (m, 1H), 2.47 (m, 9H).

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureat reflux temperature for four days
  3. filtrationFilter the mixture
  4. customevaporate the filtrate
  5. customPurify by silica gel chromatography
  6. washeluting with 0-65% EtOAc in hexanes

Sources & evidence

ORD record
ord-388efcbdfa2d47ddab62c22dabd14f3c
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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