Water → HCID 67165684, compound

HRID 552343Notes

Reaction equation

HRID 552343 reaction equation
[CH2:1]([N:8]1[C:12]2([CH2:17][CH2:16][N:15]([C:18](=[O:26])[C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)[NH:11][C@@H:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]1=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C[Si](Cl)(C)C.CCCCCC>CC(CC)=O>[ClH:25].[CH2:1]([N:8]1[C:12]2([CH2:17][CH2:16][N:15]([C:18](=[O:26])[C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[CH2:14][CH2:13]2)[NH:11][C@@H:10]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:9]1=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 67165685HCID 67165685, compound

Product 1

HCID 67165684HCID 67165684, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1,3-(S)-dibenzyl-8-(4-chlorobenzoyl)-1,4,8-triazaspiro[4,5]decan-2-one (2.6 g, 5.5 mmol) was dissolved in ethyl methyl ketone (21 mL), and water (54 μL) and TMSCl (763 μL) were added and the mixture was stirred overnight. Hexane (10 mL) was then added, and the solid matter was isolated by filtration and dried in vacuo. The precipitated solid matter was isolated by filtration and dried in vacuo. The product 1,3-(S)-dibenzyl-8-(4-chlorobenzoyl)-1,4,8-triazaspiro[4,5]decan-2-one hydrochloride was obtained in a yield of 2.53 g (90%). Examples 35 and 36 were prepared with irradiation by microwaves:

Workup

  1. customthe solid matter was isolated by filtration
  2. customdried in vacuo
  3. customThe precipitated solid matter was isolated by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1b1e3bcae38243528b9e3fd64c96cf13
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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