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(-)-Epichlorohydrin → 2-Chloro-5-[(2S)-3-chloro-2-hydroxypropyl]-N-[(4-methoxyphenyl)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

HRID 1765543
ノート
印刷プレビュー

反応式

HRID 1765543 の反応式
C([Mg]Cl)(C)C.[Cl:6][C:7]1[CH:35]=[CH:34][C:33](I)=[CH:32][C:8]=1[C:9]([N:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:10].[CH2:37]([C@@H:39]1[O:41][CH2:40]1)[Cl:38]>O1CCCC1.C(=O)(O)[O-].[Na+].O>[Cl:6][C:7]1[CH:35]=[CH:34][C:33]([CH2:40][C@H:39]([OH:41])[CH2:37][Cl:38])=[CH:32][C:8]=1[C:9]([N:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 2734062(-)-EpichlorohydrinHCID 211074122-Chloro-5-iodo-N-[(4-methoxyphenyl)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamideHCID 178418918HCID 178418918、化合物

生成物 1

HCID 211074072-Chloro-5-[(2S)-3-chloro-2-hydroxypropyl]-N-[(4-methoxyphenyl)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

試薬・触媒・溶媒 3

HCID 962Water
溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
30 °C

実験手順

iso-Propylmagnesium chloride solution (2M in tetrahydrofuran, 72.9 mL) was added to a stirred solution of 2-chloro-5-iodo-N-[(4-methoxyphenyl)methyl]-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)benzamide (Example 15a) (72.87 g) in anhydrous tetrahydrofuran (1 L) at 0° C. under nitrogen. After 30 minutes, copper(I) bromide dimethylsulphide complex (0.68 g) followed by (R)-(−)epichlorohydrin (11.4 mL) were added. The mixture was warmed to 30° C. for 2 hours then diluted with saturated sodium bicarbonate solution (1 L) and water (500 mL) then extracted with ethyl acetate (2×1 L). Organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residual oil was dissolved in methanol (600 mL), stirred overnight and the precipitated solid filtered and dried in vacuo to give the titled compound (52.25 g).

後処理

  1. additionwere added
  2. extractionthen extracted with ethyl acetate (2×1 L)
  3. dry with materialOrganic extracts were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. dissolutionThe residual oil was dissolved in methanol (600 mL)
  7. filtrationthe precipitated solid filtered
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-bb451aa354b94ec9a26569d396d3548b
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07227038B2

反応ノート

読み込み中…

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