Indene → Tert-butyl Spiro[indene-1,4'-piperidine]-1'-carboxylate

HRID 1635795Notes

Reaction equation

HRID 1635795 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:20]([O:24][C:25]([N:27]([CH2:31][CH2:32]Cl)[CH2:28][CH2:29]Cl)=[O:26])([CH3:23])([CH3:22])[CH3:21]>O1CCCC1>[C:20]([O:24][C:25]([N:27]1[CH2:31][CH2:32][C:1]2([C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 7219IndeneHCID 2733832Lithium HexamethyldisilazideHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 3653579Tert-butyl Spiro[indene-1,4'-piperidine]-1'-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 60 ml of anhydrous tetrahydrofuran, 11.6 g (0.10 mole) of indene were dissolved, followed by the gradual dropwise addition of 200 ml (0.20 mole) of lithium bistrimethylsilylamide (a 1.0M tetrahydrofuran solution) for one hour under ice cooling. After stirring the reaction mixture for 30 minutes, 50 ml of a tetrahydrofuran solution of 24.2 g (0.10 mole) of N-t-butoxycarbonyl-bis(2-chloroethyl)amine were added dropwise to the reaction mixture for 20 minutes. The resulting mixture was further stirred for 2 hours under ice cooling. The reaction mixture was distilled under reduced pressure. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=97:3), whereby 21.3 g (89%) of the title compound were obtained as white crystals.

Workup

  1. stirringThe resulting mixture was further stirred for 2 hours under ice cooling
  2. distillationThe reaction mixture was distilled under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=97:3)

Sources & evidence

ORD record
ord-d0c20202b3b84cb8b3a275e445c06bf6
Source dataset
uspto-grants-2003_01
Patent number
US06511975B1

Reaction notes

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