Sodium Thiosulfate → Benzyl methyl4-oxocyclohexylcarbamate

HRID 25654

反応式

HRID 25654 の反応式
[CH2:1]([O:8][C:9](=[O:19])[N:10]([C@H:12]1[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].[Br-].C([O-])(O)=O.[Na+].[O-]Cl.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.O.CC1(C)N([O])C(C)(C)CCC1>[CH2:1]([O:8][C:9](=[O:19])[N:10]([CH3:11])[CH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

9

反応物 5

HCID 24477Sodium ThiosulfateHCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 23665760Sodium Hypochlorite2 回HCID 178485997HCID 178485997、化合物

生成物 1

HCID 58562802Benzyl methyl4-oxocyclohexylcarbamate収率 99%

試薬・触媒・溶媒 3

HCID 2724126Tempo触媒2 回HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 2.63 g (10 mmol) of cis-(4-Hydroxy-cyclohexyl)-methyl-carbamic acid benzyl ester in 16 ml CH2Cl2 was treated with a solution 0.24 g (2 mmol) of KBr and 0.28 g (3.33 mmol) of NaHCO3 in 5 ml of water. The suspension was cooled (0-5° C.) and 8 mg (0.05 mmol) of TEMPO and then 5.7 ml (12.5 mmol) of NaOCl (13%, 2.18 M in water) were added during 20 min. After 1 h at this temperature, again 8 mg (0.05 mmol) of TEMPO and then 2.85 ml (6.25 mmol) of NaOCl (13%, 2.18 M in water) were added. After 1 h, 5 ml of 1M sodium thiosulfat solution was added. The aqueous phase was extracted with CH2Cl2(2×), the organic phase was dried (Na2SO4), filtered and evaporated to give 2.57 g (99%) of Methyl-(4-oxo-cyclohexyl)-carbamic acid benzyl ester, MS: 261 (M).

後処理

  1. extractionThe aqueous phase was extracted with CH2Cl2(2×)
  2. dry with materialthe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

出典と根拠

ORDレコード
ord-684046808ff74118b5c422a3a65be5d6
出典データセット
uspto-grants-2005_02
特許番号
US06858651B2

関連ノート

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