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

HRID 473241Notes

Reaction equation

HRID 473241 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5bf53b7eabdd4343b63fc178a92d953d
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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