Water → 3-(4,4'-Dimethoxytrityloxy)methyl-5-fluoromethylbenzylamine

HRID 473241ノート

反応式

HRID 473241 の反応式
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]([C:7]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:31]=[C:32]([CH2:34][F:35])[CH:33]=2)[CH2:27][N:28]=[N+]=[N-])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:31]=[C:32]([CH2:34][F:35])[CH:33]=2)[CH2:27][NH2:28])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2[CH:36]=[CH:37][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866715193-(4,4'-Dimethoxytrityloxy)methyl-5-fluoromethylbenzylazide

生成物 1

HCID 672535713-(4,4'-Dimethoxytrityloxy)methyl-5-fluoromethylbenzylamine収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-(4,4′-dimethoxytrityloxy)methyl-5-fluoromethylbenzylazide (39) (247 mg, 0.50 mmol) in THF (5.00 mL) were added water (0.20 mL) and then triphenylphosphine (264 mg, 1.01 mmol). The air was evacuated from the reaction system, and then Ar was charged therein. The reaction mixture was stirred for 15 hours at a room temperature. TLC was used to confirm the progress of the reaction. Then, the reaction mixture was extracted with EtOAc. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. The residue was purified by neutral silica gel column chromatography (EtOAc, then EtOAc: MeOH=2:1) to isolate 3-(4,4′-dimethoxytrityloxy)methyl-5-fluoromethylbenzylamine (40) (234 mg, 100%) as a white opaque oil.

後処理

  1. customThe air was evacuated from the reaction system
  2. additionAr was charged
  3. customthe progress of the reaction
  4. extractionThen, the reaction mixture was extracted with EtOAc
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by neutral silica gel column chromatography (EtOAc

出典と根拠

ORDレコード
ord-5bf53b7eabdd4343b63fc178a92d953d
出典データセット
uspto-grants-2014_01
特許番号
US08633304B2

反応ノート

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