Dichloromethane → 1-(4-Chlorobenzyl)-7-cyclohexyl-1,7-diazaspiro[4.4]nonane-3,6-dione

HRID 1672394Notes

Reaction equation

HRID 1672394 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:47]=[CH:46][C:27]([CH2:28][N:29]2[C:33]3([CH2:37][CH2:36][N:35]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[C:34]3=[O:44])[CH2:32][C@@H:31]([OH:45])[CH2:30]2)=[CH:26][CH:25]=1.C(Cl)Cl.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:29]2[C:33]3([CH2:37][CH2:36][N:35]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[C:34]3=[O:44])[CH2:32][C:31](=[O:45])[CH2:30]2)=[CH:46][CH:47]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 24759088(3R)-1-(4-chlorobenzyl)-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]nonan-6-one

Product 1

HCID 673556101-(4-Chlorobenzyl)-7-cyclohexyl-1,7-diazaspiro[4.4]nonane-3,6-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin periodinane (0.19 g, 0.00044 mol) was added to a solution of (3R)-1-(4-chloro-benzyl)-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]nonan-6-one (0.080 g, 0.00022 mol; prepared as in Example 32, derived from peak 2 of step 2) in DCM (2.0 mL, 0.031 mol). The resulting mixture was stirred for 3 h at RT. The mixture was then diluted with ethyl acetate and stirred with Na2S2O3 followed by saturated NaHCO3. Following separation of the organic and aqueous layers, the organic layer was dried and concentrated in vacuo to afford the desired product. LC/MS: 361.1 (M+1H)+.

Workup

  1. customseparation of the organic and aqueous layers
  2. customthe organic layer was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc94199668de46c0b408adcca1ae4642
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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