Water → HCID 10690894, compound

HRID 2373092Notes

Reaction equation

HRID 2373092 reaction equation
C(=O)(O[CH2:10][C:11]1([Si](C)(C)C)[C:23]2[CH:22]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][C:14]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:15][CH:16]=2)NC1C=CC=CC=1.O.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[C:24]([C:21]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:15][CH:16]=3)[CH:11]([CH2:10][N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[C:23]=2[CH:22]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 3

HCID 962WaterHCID 8082Piperidine2×HCID 53845348HCID 53845348, compound

Product 1

HCID 10690894HCID 10690894, compoundYield 100%

Procedure

Piperidine Cleavage of 2,7-Di-tert-butyl-9-trimethylsilyl-9-fluorenylmethyl Carbanilate: A solution of 0.4 g of DT-Fmoc-analine in 8.0 mL of piperidine was stirred at room temperature for 22 hours. The mixture was poured into 50 mL of cold water and stirred for 10 minutes. The precipitate was removed by filtration, rinsed with water (2×5 mL), and dried in air to afford 0.30 g (100%) of crude N-(2,7-di-tert-butyl-9-fluorenylmethyl)piperidine as an off-white solid. Recrystallization from CH3OH--CHCl3 (2:1) gave 0.248 g (82.53%) of the pure amine as white crystals, m.p. 159°-160° C., identified by mixture melting point, and IR and NMR spectral comparison with a sample obtained by piperidine cleavage of DT-Fmoc-PCA.

Workup

  1. customThe precipitate was removed by filtration
  2. washrinsed with water (2×5 mL)
  3. customdried in air

Sources & evidence

ORD record
ord-0e51eb81513e4b03bb303be56feee6a3
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

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