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

HRID 1672394노트

반응식

HRID 1672394 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-fc94199668de46c0b408adcca1ae4642
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998959B2

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