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Sodium Chloride → 3-Benzyl-1 oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid tert-butyl ester

HRID 1619739
ノート
印刷プレビュー

反応式

HRID 1619739 の反応式
[C:1]1([CH2:7][C:8](Cl)=[N:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22](=[CH2:25])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.[Cl-].[Na+]>O.C(Cl)Cl>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22]2([O:10][N:9]=[C:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:25]2)[CH2:21][CH2:20]1)=[O:18])([CH3:14])([CH3:13])[CH3:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 27568081-Boc-4-MethylenepiperidineHCID 73177631HCID 73177631、化合物

生成物 1

HCID 598303913-Benzyl-1 oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒
3 回

実験手順

Compound W (3.33 g, 20 mmol), dissolved in abs. DCM (15 ml), was added dropwise at 0° C. within 10 min to a solution of compound B (2.81 g, 14.3 mmol in abs. DCM (22 ml)). A solution of triethylamine (11.2 ml, 80 mmol) in abs. DCM (10 ml) was added to this mixture at 0° C. within 10 min. As the reaction was highly exothermic, cooling was carried out with a mixture of ice and sodium chloride. The reaction mixture was stirred for 16 h at RT. For working up the mixture, DCM (15 ml) and water (45 ml) were added and the mixture was stirred for 15 min. After separation of the phases, the aqueous phase was extracted with DCM (2×45 ml). The phases were separated. The organic phase was washed successively with 10% citric acid solution (2×30 ml) and sat. NaCl solution (30 ml). The organic phase was dried and concentrated (5.3 g, brown oil). The residue was separated by chromatography [silica gel 60 (180 g); cyclohexane/EtOAc 7:1 (1,200 ml); 5:1 (900 ml)]. The desired product X was obtained in a yield of 681 mg (11%).

後処理

  1. temperaturecooling
  2. additionwere added
  3. stirringthe mixture was stirred for 15 min
  4. customAfter separation of the phases
  5. extractionthe aqueous phase was extracted with DCM (2×45 ml)
  6. customThe phases were separated
  7. washThe organic phase was washed successively with 10% citric acid solution (2×30 ml) and sat. NaCl solution (30 ml)
  8. customThe organic phase was dried
  9. concentrationconcentrated (5.3 g, brown oil)
  10. customThe residue was separated by chromatography [silica gel 60 (180 g); cyclohexane/EtOAc 7:1 (1,200 ml); 5:1 (900 ml)]

出典と根拠

ORDレコード
ord-5e17e3200df649e4a36ead3336ae956f
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08772307B2

反応ノート

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