Ammonium Chloride → HCID 69307765, compound

HRID 2056742Notes

Reaction equation

HRID 2056742 reaction equation
Br[C:2]1[C:12]2[C:13]3[C:5]([CH:6]=[CH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.C([Li])CCC.[O:19]=[C:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.[Cl-].[NH4+]>C1COCC1>[CH2:7]1[C:8]2=[C:13]3[C:12](=[CH:11][CH:10]=[CH:9]2)[C:2]([C:20]2([OH:19])[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:24][CH2:25]2)=[CH:3][CH:4]=[C:5]3[CH2:6]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 122444035-BromoacenaphthyleneHCID 178418339Butyllithium

Product 1

HCID 69307765HCID 69307765, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromoacenaphthylene (1.00 g, 4.29 mmol) in dry THF (20 mL), under nitrogen at −78° C., was added a solution of n-butyllithium (2.5M in hexanes) (1.89 mL, 4.72 mmol) over a period of 30 min. The resulting deep red solution was left to stir for a further 30 minutes at −78° C. A solution of tert-butyl 4-oxo-1-piperidinecarboxylate (0.94 g, 4.72 mmol) in dry THF (10 mL) was then added over 30 min. After 2.5 h a cooled solution of saturated ammonium chloride (30 mL) was added, the reaction mixture allowed to warm to room temperature and then extracted with diethyl ether. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to yield a thick, yellowish tan oil. This oil was purified by flash chromatography on silica, eluting with a methanol/dichloromethane gradient, to yield tert-butyl 4-(1,2-dihydro-5-acenaphthylenyl)-4-hydroxy-1-piperidinecarboxylate as a sticky yellow residue.

Workup

  1. waitThe resulting deep red solution was left
  2. temperatureto warm to room temperature
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a thick, yellowish tan oil
  7. customThis oil was purified by flash chromatography on silica
  8. washeluting with a methanol/dichloromethane gradient

Sources & evidence

ORD record
ord-e075035d844c49a59bb5b73250aa9a50
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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