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Triphenylphosphine → ({(1S,2S,4R)-4-azido-2-[(benzyloxy)methyl]cyclopentyl}-oxy)(tert-butyl)dimethylsilane

HRID 1397550
ノート
印刷プレビュー

反応式

HRID 1397550 の反応式
[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:13][C@@H:12](O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1C=CC(OP(OC2C=CC=CC=2)([N:64]=[N+:65]=[N-:66])=O)=CC=1>C1COCC1>[N:64]([C@H:12]1[CH2:13][C@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11]1)=[N+:65]=[N-:66]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 123414Diphenylphosphoryl azideHCID 5462977Diethyl azodicarboxylateHCID 66798092(1S,3S,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanol

生成物 1

HCID 86618712({(1S,2S,4R)-4-azido-2-[(benzyloxy)methyl]cyclopentyl}-oxy)(tert-butyl)dimethylsilane収率 63%

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (1S,3S,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)-silyl]oxy}cyclopentanol (138.9 mg, 0.0004127 mol) and PPh3 (118 mg, 0.000451 mol) in THF (2.7 mL) at 0° C. was slowly added DEAD (71.1 μL, 0.000451 mol). The reaction was stirred for 5 minutes, then diphenylphosphonic azide (97.4 μL, 0.000452 mol) was added dropwise. The mixture was stirred for one hour. The reaction was partitioned with water and EtOAc. The layers were separated and the aqueous extracted with EtOAc (2×). The combined organics were washed with brine (1×), dried (Na2SO4), filtered, and collected in vacuo. The residue was purified by flash chromatography (0 to 10% EtOAc/hexanes) to obtain 93.5 mg (63%) of the title compound.

後処理

  1. customat 0° C.
  2. stirringThe mixture was stirred for one hour
  3. customThe reaction was partitioned with water and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous extracted with EtOAc (2×)
  6. washThe combined organics were washed with brine (1×)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customcollected in vacuo
  10. customThe residue was purified by flash chromatography (0 to 10% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-1b588623dfe24a03b595996b5b31f881
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901136B2

反応ノート

読み込み中…

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