Ethanol → 4-(1-Fmoc-piperidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2263908Notes

Reaction equation

HRID 2263908 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]([N:31]1[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]1)([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15].C(O)C.C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:34]2[CH2:33][CH2:32][N:31]([C:14]([O:16][CH2:17][CH:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:25]4[C:30]3=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:15])[CH2:36][CH2:35]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 7363031-Fmoc-4-piperidoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 670713454-(1-Fmoc-piperidin-4-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 20.7%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolvent

Procedure

N-tert-butoxycarbonyl-piperazine (1.86 g, 10 mmol, Lancaster), N-Fmoc-4-oxo-piperidine (3.21 g, 10 mmol, Aldrich) and titanium(IV) isopropoxide (3.72 mL, Aldrich) were combined, and the mixture was stirred at room temperature for 1 h. Then ethyl alcohol (10 mL) was added followed by sodium cyanoborohydride (0.47 g, 7.48 mmol, Aldrich), and the mixture was stirred overnight. Water (2 mL) was added and the mixture was filtered. The solid was washed with ethyl alcohol and the filtrate was combined. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (ISCO machine, silica gel, eluting with 20% ethyl acetate in hexane for a period of 30 min) to give 4-(1-Fmoc-piperidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester as a white foam (1.02 g).

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationthe mixture was filtered
  3. washThe solid was washed with ethyl alcohol
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash chromatography (ISCO machine, silica gel
  6. washeluting with 20% ethyl acetate in hexane for a period of 30 min)

Sources & evidence

ORD record
ord-9703083b6f7840f3b8497ec9ffc44170
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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