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1-(Bromomethyl)-3-chlorobenzene → 4-(3-Chlorobenzyl)-4-(2-methylpropane-2-sulphinylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2405997
ノート
印刷プレビュー

反応式

HRID 2405997 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([S:19]([NH2:21])=[O:20])([CH3:18])([CH3:17])[CH3:16].[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[CH2:26][Mg]Br.ClC1C=C(C=CC=1)CBr.[Mg]>C1COCC1.[Cl-].[Na+].O.C(OCC)(=O)C.C(OCC)C.[Cl-].[NH4+].[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:26][C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([Cl:22])[CH:24]=2)([NH:21][S:19]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:20])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

12

反応物 5

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 3382465Tert-ButanesulfinamideHCID 5462224MagnesiumHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 178478084HCID 178478084、化合物

生成物 1

HCID 668730384-(3-Chlorobenzyl)-4-(2-methylpropane-2-sulphinylamino)-piperidine-1-carboxylic acid tert-butyl ester
収率 31.5%

試薬・触媒・溶媒 6

HCID 76524Titanium tetraethoxide触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of N—BOC-piperidone (0.205 g, 1.03 mmol), t-butylsulphinamide (0.13 g, 1.07 mmol) and titanium tetraethoxide (0.42 ml, 2.0 mmol) in dry THF (5 ml) was refluxed under nitrogen for 5 h. The cooled solution was diluted with brine (10 ml) and ethyl acetate (10 ml). The suspension was shaken, the filtered through Celite, washing with ethyl acetate (10 ml). The two-phase filtrate was separated and the organic layer was dried (Na2SO4) filtered and concentrated to give the crude sulphinimine (0.293 g). The crude sulphinimine (0.293 g) was suspended in dry THF (2 ml) and stirred at room temperature under nitrogen. A solution of 3-chlorobenzyl magnesium bromide (ca. 4 mmol) (freshly prepared as a solution in diethyl ether from 3-chlorobenzylbromide and magnesium turnings) was added to give an orange solution. After 3 hours, the mixture was diluted with saturated aqueous ammonium chloride (20 ml) and extracted with ethyl acetate (20 ml). The extract was washed with water (20 ml), brine (10 ml), dried (Na2SO4), filtered and concentrated. Flash column chromatography, eluting with 50% ethyl acetate-hexanes, gave 4-(3-chlorobenzyl)-4-(2-methylpropane-2-sulphinylamino)-piperidine-1-carboxylic acid tert-butyl ester as a straw-coloured foam (0.139 g, 0.324 mmol, 31%). LC-MS (LCT) m/z 451, 453 [M+Na+], Rt 8.22 min.

後処理

  1. filtrationthe filtered through Celite
  2. washwashing with ethyl acetate (10 ml)
  3. customThe two-phase filtrate was separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude sulphinimine (0.293 g)
  8. stirringstirred at room temperature under nitrogen
  9. additionwas added
  10. customto give an orange solution
  11. extractionextracted with ethyl acetate (20 ml)
  12. washThe extract was washed with water (20 ml), brine (10 ml)
  13. dry with materialdried (Na2SO4)
  14. filtrationfiltered
  15. concentrationconcentrated
  16. washFlash column chromatography, eluting with 50% ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-f38da22c15124c7d81a607b23ab02860
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08809336B2

反応ノート

読み込み中…

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