Triethylamine → 4-(3-((Tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholine

HRID 1487195Notes

Reaction equation

HRID 1487195 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[C:11]([CH2:13][OH:14])[CH:12]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[Si:29]([O:14][CH2:13][C:11]1[CH:12]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:8]=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 9878047(5-Morpholin-4-YL-2-nitro-phenyl)-methanol

Product 1

HCID 866996854-(3-((Tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholineYield 90.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (5-morpholino-2-nitrophenyl)methanol (3.0 g, 12.6 mmol), triethylamine (2.54 g, 25.2 mmol) and 4-dimethylaminopyridine (0.2 g) in dichloromethane (100 mL) was added tert-butylchlorodimethylsilane (2.83 g, 18.9 mmol). After the addition was over, the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, and the organic phase was washed by saturated sodium bicarbonate, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 4-(3-((tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholine (4.0 g, yield 90.9%).

Workup

  1. additionAfter the addition
  2. washthe organic phase was washed by saturated sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ccaa05a926ba49a38405e9ef64798303
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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