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Methyl iodide → tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate

HRID 908450
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HRID 908450 반응식
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:9]([CH2:19][OH:20])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:26]>CN(C=O)C>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[C@@H:9]([CH2:19][O:20][CH3:26])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14117005(2R,4R)-tert-Butyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 67388742tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
20 °C

실험 절차

A solution of tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (9.32 g) in DMF (15 ml) was added to a stirred suspension of sodium hydride (60% dispersion) (1.37 g) in DMF 100 ml) at −10° C. Iodomethane (2.13 ml) was added and the reaction allowed to warm to 20° C. The reaction mixture was quenched carefully with water and evaporated to dryness. The crude material was partitioned between ethyl acetate (250 ml) and water (100 ml). The organic layer was washed with brine (100 ml), dried over Magnesium sulphate, filtered and evaporated to give tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate (6.68 g) as a colourless oil. NMR Spectrum: (DMSOd6) 0.02 (6H, s); 0.83-0.84 (9H, s); 1.36 (9H, s); 1.78 (1H, d); 1.99 (1H, s); 2.99 (1H, d); 3.19 (3H, d); 3.23-3.48 (3H, m); 3.80 (1H, s); 4.33 (1H, s).

후처리

  1. customThe reaction mixture was quenched carefully with water
  2. customevaporated to dryness
  3. customThe crude material was partitioned between ethyl acetate (250 ml) and water (100 ml)
  4. washThe organic layer was washed with brine (100 ml)
  5. dry with materialdried over Magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-926cfebca1c54243a01a8b13c6509e5f
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017611B2

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