Anisole → HCID 21839966, compound

HRID 2256027Notes

Reaction equation

HRID 2256027 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])(C)(C)C.[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCCCCC.C(OCC)(=O)C>O1CCCC1.CCCCC.O>[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([OH:30])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[O:7][CH3:8])[CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 7519AnisoleHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 21226206Ethyl acetate hexaneHCID 178418306HCID 178418306, compound

Product 1

HCID 21839966HCID 21839966, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of anisole (2.19 g) in tetrahydrofuran (50 mL) was cooled to -78° C. and treated with tert-butyl lithium (12 mL of a 1.7M solution in pentane). The resulting reaction mixture was warmed to -15° C. and stirred for 45 minutes. The reaction mixture was cooled back to -78° C. and treated with a solution of 1-benzyloxycarbonyl-4-piperidone (4.67 g) in tetrahydrofuran (5 mL). The reaction mixture was warmed to -15° C. and stirred for 1 hour before it was allowed to reach ambient temperature and stirred for 72 hours. The reaction mixture was diluted with water, and extracted several times with ethyl acetate. The combined organic layers were dried and evaporated to afford the crude product. Chromatography, with hexane:ethyl acetate (2:1) as the eluent, gave a mixture of the alcohol and starting material (2.98 g); NMR (CDCl3): 1.95-2.04 (m, 4), 2.9 (broad, 2), 3.90 (s, 3), 5.15 (s, 2), 6.93-6.99 (m, 2), 7.21-7.36 (m, 7); MS: m/z=342(M+1). This material was used in the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled back to -78° C.
  3. temperatureThe reaction mixture was warmed to -15° C.
  4. stirringstirred for 1 hour before it
  5. customto reach ambient temperature
  6. stirringstirred for 72 hours
  7. extractionextracted several times with ethyl acetate
  8. customThe combined organic layers were dried
  9. customevaporated
  10. customto afford the crude product
  11. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-92ae8c5d156948ffaac98891bae52e6a
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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