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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
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HRID 1765543 반응식
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]
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참가 물질

7

반응물 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, 화합물

생성물 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

시약·촉매·용매 3

HCID 962Water
용매
HCID 8028Tetrahydrofuran용매
HCID 516892Sodium Bicarbonate용매

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온도
30 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bb451aa354b94ec9a26569d396d3548b
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07227038B2

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