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Azide → (1R,2R,6S)-6-amino-2-[tert-butyl(dimethyl)silyl]oxy-2-methyl-cyclohexanol

HRID 527010
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HRID 527010 반응식
[N-]=[N+]=[N-].[N:4]([C@H:7]1[CH2:12][CH2:11][CH2:10][C@:9]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])([CH3:13])[C@@H:8]1[OH:22])=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:4][C@H:7]1[CH2:12][CH2:11][CH2:10][C@:9]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])([CH3:13])[C@@H:8]1[OH:22]
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참가 물질

6

반응물 3

HCID 33558AzideHCID 86667433(1R,2R,3S)-3-azido-1-(tert-butyldimethylsilyloxy)-1-methylcyclo-hexan-2-olHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 68007680(1R,2R,6S)-6-amino-2-[tert-butyl(dimethyl)silyl]oxy-2-methyl-cyclohexanol

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 8857
Ethyl Acetate
용매

실험 절차

A solution of azide, 50d, (0.25 g; 0.89 mmol) in 20 mL of ethyl acetate was hydrogenated with Degussa palladium (20 mole %) under 1 atmosphere of hydrogen overnight. The reaction mixture was filtered over celite and the celite was eluted with 2×10 mL of EtOAc. The filtrate was concentrated in vacuo to afford 230 mg of an oil that was used directly for the next step without further purification.

후처리

  1. filtrationThe reaction mixture was filtered over celite
  2. washthe celite was eluted with 2×10 mL of EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-08b25f2b51ec4353bc9e5b903ef312f3
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09345708B2

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