tert-Butyl carbazate → 9H-Fluoren-9-ylmethyl 4-[(t-butoxycarbonyl)hydrazono]piperidine-1-carboxylate

HRID 550377Notes

Reaction equation

HRID 550377 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:25]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:28])[NH:26][NH2:27]>C(O)C>[C:30]([O:29][C:25]([NH:26][N:27]=[C:21]1[CH2:20][CH2:19][N:18]([C:16]([O:15][CH2:14][CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[O:17])[CH2:23][CH2:22]1)=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 7363031-Fmoc-4-piperidone

Product 1

HCID 183211409H-Fluoren-9-ylmethyl 4-[(t-butoxycarbonyl)hydrazono]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[(9H-fluoren-9-yl)methyloxycarbonyl]-4-piperidone (16.0 g, 50.0 mmol) and tert-butyl carbazate 7.25 g, 55.5 mmol) in ethanol (250 mL) was refluxed for 1 h. The solution was cooled and concentrated. Addition of ether (100 mL) produced the title compound as a white precipitate (21.0 g). 1H NMR (500 MHz, CDCl3) δ 7.77 (d, J=7 Hz, 2H), 7.57 (d, J=7 Hz, 2H), 7.40 (t, J=7 Hz, 2H), 7.32 (t, J=7 Hz, 2H), 4.50 (br s, 2H), 4.24 (t, J=6 Hz, 1H), 3.4-3.7 (br m, 4H), 2.47 (br s, 2H), 2.2-2.1 (br m, 2H), 1.56 (s, 9H).

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. additionAddition of ether (100 mL)

Sources & evidence

ORD record
ord-e7e3628a4eaf4ae6998c1f53c45bcce3
Source dataset
uspto-grants-2011_05
Patent number
US07947678B2

Reaction notes

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