Hydrochloric Acid → HCID 67421015, compound

HRID 2365922Notes

Reaction equation

HRID 2365922 reaction equation
C([Li])CCC.[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](I)=[CH:16][C:15]=1[F:29])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:30]([N:37]1[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]1)([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].[Cl-].[NH4+].Cl>CCCCCC.O1CCCC1>[C:33]([O:32][C:30]([N:37]1[CH2:42][CH2:41][CH:40]([C:17]2[CH:16]=[C:15]([F:29])[C:14]([O:13][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:19][C:18]=2[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:39][CH2:38]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 70921801HCID 70921801, compoundHCID 178418339Butyllithium

Product 1

HCID 67421015HCID 67421015, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

4.0 ml (9.9 mmol, 1.2 eq) of 2.5M n-butyllithium in hexane are added to a solution of 3.59 g (8.26 mmol, 1 eq) of 1,5-bis(benzyloxy)-2-fluoro-4-iodobenzene in 40 ml of tetrahydrofuran, cooled to −70° C. The reaction medium is stirred at −70° C. for 25 minutes and 1.97 g (9.9 mmol, 1.2 eq) of 1-boc-4-piperidone in solution in 20 ml of tetrahydrofuran are added. The reaction medium is stirred at −70° C. for 1 hour and is then left to return to ambient temperature overnight. 30 ml of a saturated solution of ammonium chloride, to which 4 ml of 2M hydrochloric acid have been added, are added to the reaction medium, which is stirred for 20 minutes and is then extracted with ethyl acetate. The organic phases are combined, dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel, elution being carried out with 95/5 heptane/ethyl acetate then 75/25 heptane/ethyl acetate (with 0.1% of TEA).

Workup

  1. stirringThe reaction medium is stirred at −70° C. for 1 hour
  2. waitis then left
  3. waitto return to ambient temperature overnight
  4. additionare added to the reaction medium, which
  5. stirringis stirred for 20 minutes
  6. extractionis then extracted with ethyl acetate
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-84e9436e80054aa5a2e053a7914f2d3e
Source dataset
uspto-grants-2014_04
Patent number
US08697726B2

Reaction notes

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