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

HRID 1782684Notes

Reaction equation

HRID 1782684 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.[NH:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH2:26]>C(O)C>[CH3:31][C:30]([CH3:33])([O:29][C:27]([NH:25][N:26]=[C:21]1[CH2:22][CH2:23][N:18]([C:16]([O:15][CH2:14][CH:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:17])[CH2:19][CH2:20]1)=[O:28])[CH3:32]

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 mixture of 16.0 g (0.05 mol) of 1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinone, 7.25 g (0.055 mol) of tert. butyl hydrazinoformate and 250 ml of ethanol was refluxed for 1 hour. The solvent was distilled off in vacuo, the oily residue remaining was triturated with diethylether. The crystalline precipitate thus formed was suction filtered and washed with a little diethylether. After the product had been dried in vacuo 21.7 g (99.7% of theory) of colourless crystals were obtained, m.p. 156-158° C. (decomposition).

Workup

  1. temperaturewas refluxed for 1 hour
  2. distillationThe solvent was distilled off in vacuo
  3. customthe oily residue remaining was triturated with diethylether
  4. customThe crystalline precipitate thus formed
  5. filtrationfiltered
  6. washwashed with a little diethylether
  7. customAfter the product had been dried in vacuo 21.7 g (99.7% of theory) of colourless crystals
  8. customwere obtained

Sources & evidence

ORD record
ord-70823f437a944b05a91f156fe600ec4b
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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