Sodium Chloride → ((1R,4S)-4-Azido-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane

HRID 402533

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HRID 402533 반응식
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C@@H:7]1[CH2:11][C@H:10](OC(=O)C)[CH:9]=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].O[C@@H]1C[C@H](OC(=O)C)C=C1.[N-:28]=[N+:29]=[N-:30].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Na+]>O1CCCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:28]([C@H:10]1[CH2:11][C@@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])[CH:8]=[CH:9]1)=[N+:29]=[N-:30]

참가 물질

9

반응물 5

HCID 5234Sodium ChlorideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 98554984-Cyclopentene-1,3-diol, 1-acetate, (1R,3S)-rel-HCID 10999690(1S,4R)-4-{[Tert-butyl(dimethyl)silyl]oxy}-2-cyclopenten-1-YL acetate

생성물 1

HCID 86639599((1R,4S)-4-Azido-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane수율 80.7%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
50 °C

실험 절차

The title compound was prepared by combining a solution of 630 mg (2.46 mmol) of acetic acid (1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester [synthesized by silylation of commercially available acetic acid (1S,4R)-4-hydroxy-cyclopent-2-enyl ester (Curran, et al. Tetrahedron 1997, 53, 1983-2004)] in 6 mL tetrahydrofuran with a solution of 320 mg (4.91 mmol) of sodium azide in 1.3 mL of water. To this biphasic mixture was added a solution of 112 mg (0.12 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 258 mg (0.98 mmol) of triphenylphosphine in 2 mL tetrahydrofuran, and the reaction mixture was heated to 50° C. for 6 h, when the reaction was complete. Sat. sodium chloride solution was added, and the aqueous phase was repeatedly extracted with ether. The combined organic phase was dried over sodium sulfate, filtered and evaporated. The crude material was purified by silica gel chromatography to yield 475 mg of the title compound (35). 1H NMR (400 MHz, DMSO) δ=0.09 (s, 3H), 0.10 (s, 3H), 0.88 (s, 9H), 1.49 (dt, J=3.9, 14.0 Hz, 1H), 2.69 (dt, J=7.4, 14.1 Hz, 1H), 4.22-4.26 (m, 1H), 4.75-4.79 (m, 1H), 5.92-5.95 (m, 1H), 6.05 (dt, J=1.8, 5.4 Hz, 1H)

후처리

  1. customThe title compound was prepared
  2. extractionthe aqueous phase was repeatedly extracted with ether
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-a54799bee101414789cc10a2d67d3e39
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742116B2

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