Diethyl Ether → HCID 178461848, compound

HRID 1487308Notes

Reaction equation

HRID 1487308 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:17][C:18]1([CH3:32])[C:23](=O)[CH2:22][CH2:21][N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19]1.C(OCC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:17][C:18]1([CH3:32])[CH2:19][N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:22]/[C:23]/1=[N:9]\[C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 6431891-Phenethylamine, (+)-HCID 22278899tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 178461848HCID 178461848, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-1-phenylethanamine (2.56 g, 21.12 mmol) and triethylamine (14.7 mL, 106 mmol) in dichloromethane (40 mL) was cooled in an ice bath and titanium tetrachloride (8.80 mL, 8.80 mmol) was added dropwise giving a light brown mixture. The cold bath was removed and tert-butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate (4.00 g, 17.60 mmol) was added as solid in one portion and the resulting mixture was allowed to stir at rt overnight. To the resulting mixture was added 75 mL of diethyl ether and the mixture was stirred at rt for 15 min then filtered through a pad of CELITE® to remove the solids and the filter cake was rinsed with additional ether (30 mL×2). The resulting clear yellow filtrate was concentrated on a rotovap to afford a yellow liquid as the title compound (5.80 g, 17.6 mmol, quantitative). This material was used directly without any further purification.

Workup

  1. customgiving a light brown mixture
  2. customThe cold bath was removed
  3. stirringthe mixture was stirred at rt for 15 min
  4. filtrationthen filtered through a pad of CELITE®
  5. customto remove the solids
  6. washthe filter cake was rinsed with additional ether (30 mL×2)
  7. concentrationThe resulting clear yellow filtrate was concentrated on a rotovap

Sources & evidence

ORD record
ord-3965328fe3014e07944615cef12047ef
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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