Ammonium Hydroxide → HCID 19097414, compound

HRID 486077Notes

Reaction equation

HRID 486077 reaction equation
[CH3:1][CH:2]1[C:7]2([CH3:11])[CH:8]([CH3:10])[CH2:9][CH:4]([C:5](C(OCC)=O)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:6]2)[N:3]1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[NH4+].[OH-]>C(N(CC)CC)C>[CH3:1][CH:2]1[C:7]([CH3:11])([CH2:6][CH2:5][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]([CH3:10])[CH2:9][CH2:4][N:3]1[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 19097404HCID 19097404, compound

Product 1

HCID 19097414HCID 19097414, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of diethyl 3,4,8-trimethyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]octane-6,6-dicarboxylate (3.4 g, 8.8 mmol) formic acid (3 mL) and triethylamine (4 mL) was heated to 160° C. for 1.5 hours. The reaction mixture was cooled to room temperature and allowed to stand for 24 hours. The mixture was basified with concentrated NH4OH and the mixture was extracted with ether (3X). The organic layers were combined, dried over anhydrous MgSO4 and concentrated in vacuo to afford 2.6 g (93%) of ethyl 2,3,4-trimethyl-1-(phenylmethyl)-3-piperidinepropanoate as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ether (3X)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2b71200150f4d78afc10d1a22b1e5bc
Source dataset
uspto-grants-1994_03
Patent number
US05290796

Reaction notes

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