Ethanol → 4-(3-Quinuclidinyl)piperazine-1-carboxylic acid, 1,1-dimethylethyl ester

HRID 494011Notes

Reaction equation

HRID 494011 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=O.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(O)C.C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([N:20]1[CH2:19][CH2:18][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:22][CH2:21]1)[CH2:2]2

Participants

7

Reactant 4

HCID 702EthanolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5661191-azabicyclo[2.2.2]octan-2-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 910215394-(3-Quinuclidinyl)piperazine-1-carboxylic acid, 1,1-dimethylethyl esterYield 42%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolvent

Procedure

1 g (8 mM) of quinuclidinone, 1.63 g (8.75 mM) of 1-piperazinecarboxylic acid t-butyl ester (1-Boc-piperazine) and 2.71 ml (9.1 mM) of titanium isopropoxide are mixed and this mixture is kept under agitation for 1 hour. 5 ml of ethanol and then 460 mg (7.3 mM) of sodium cyanoborohydride are then added, and this mixture is agitated for 24 hours at ambient temperature. 25 ml of water are added and agitation is carried out for 15 minutes. The precipitate formed is separated off by filtration and the filtrate is concentrated under reduced pressure. The residue is purified by NH2 silica gel chromatography in eluting with the aid of a toluene/isopropanol mixture (95/5; v/v). 1 g of the compound sought after are thus obtained as a white solid (yield=42%).

Workup

  1. waitagitation is carried out for 15 minutes
  2. customThe precipitate formed
  3. customis separated off by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by NH2 silica gel chromatography
  6. washin eluting with the aid of a toluene/isopropanol mixture (95/5; v/v)

Sources & evidence

ORD record
ord-e5a115c959e44ff1b082c015be20cf54
Source dataset
uspto-grants-2009_05
Patent number
US07538111B2

Reaction notes

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