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Imidazole → 4-(Tert-butyl-dimethyl-silanyloxymethyl)-1-cycloheptyl-pyrrolidine-2-one

HRID 2115598
ノート
印刷プレビュー

反応式

HRID 2115598 の反応式
[BH4-].[Na+].CO[C:5]([CH:7]1[CH2:11][C:10](=O)[N:9]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:8]1)=O.[OH:20]P(O)(O)=O.N1C=CN=C1.[C:30]([Si:34](Cl)(C)C)([CH3:33])([CH3:32])[CH3:31].C([O:41][CH2:42][CH3:43])(=O)C>CO.O1CCCC1>[C:30]([SiH2:34][O:20][C:7]([CH3:8])([CH3:5])[CH:11]1[CH2:10][N:9]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:42](=[O:41])[CH2:43]1)([CH3:33])([CH3:32])[CH3:31]
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

9

反応物 6

HCID 795ImidazoleHCID 1004Phosphoric AcidHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 4311764Sodium borohydrideHCID 666569581-Cycloheptyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

生成物 1

HCID 131727092
4-(Tert-butyl-dimethyl-silanyloxymethyl)-1-cycloheptyl-pyrrolidine-2-one

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

Sodium borohydride (0.213 g, 5.77 mmoles) was added to a solution of Example 1A (0.7 g, 2.92 mmoles) in methanol (3 mL) and tetrahydrofuran (3 mL) and stirred at 60° C. for two hours. The reaction was cooled to 0° C. and O-phosphoric acid (1.6 g, 17.4 mmoles) was added and stirred. The reaction was filtered through a pad of celite, rinsed with methanol, and concentrated under vacuo. The crude oil was taken up in ethyl acetate (25 mL) and washed with water (25 mL). The organic layer was dried with MgSO4, filtered and evaporated in vacuo. The resulting oil was taken up in N,N-dimethylformamide (4 mL) and imidazole (391 g, 5.76 mmoles) and Tert-butyl-chloro-dimethyl-silane (583 g, 3.88 mmoles) were added and stirred for three hours. The reaction was diluted with ethyl acetate (40 mL) and washed with water (50 mL) and brine (25 mL). The organic layer was dried with MgSO4 filtered and evaporated in vacuo. The crude product was purified by flash chromatography (hexanes:ethyl acetate 95:5 to 75:25) to give the title compound as a colorless oil.

後処理

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringstirred
  3. filtrationThe reaction was filtered through a pad of celite
  4. washrinsed with methanol
  5. concentrationconcentrated under vacuo
  6. washwashed with water (25 mL)
  7. dry with materialThe organic layer was dried with MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. stirringstirred for three hours
  11. washwashed with water (50 mL) and brine (25 mL)
  12. dry with materialThe organic layer was dried with MgSO4
  13. filtrationfiltered
  14. customevaporated in vacuo
  15. customThe crude product was purified by flash chromatography (hexanes:ethyl acetate 95:5 to 75:25)

出典と根拠

ORDレコード
ord-1a128a5192af43cda51ebde3c80bd194
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07435833B2

反応ノート

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