Imidazole → N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)-2,2,2-trifluoroacetamide

HRID 605852Notes

Reaction equation

HRID 605852 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@H:9]([OH:16])[CH2:8][CH2:7]1)=[O:4].N1C=CN=C1.CN(C=O)C.[C:29]([Si:33](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:32])([CH3:31])[CH3:30]>CCOC(C)=O>[Si:33]([O:16][C@H:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:6]([NH:5][C:3](=[O:4])[C:2]([F:17])([F:18])[F:1])[CH2:7][CH2:8]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 597048682,2,2-Trifluoro-N-((1R,4R)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Product 1

HCID 59704873N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)-2,2,2-trifluoroacetamideYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 250 ml round bottom flask containing 2.2 g (8.49 mmol) of 2,2,2-trifluoro-N-((1R,4R)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide and 1.73 g (25.48 mmol) of imidazole was added 35 ml of DMF, and stirring was started. To this solution was added 4.67 g (16.99 mmol) of t-butylchlorodiphenylsilane. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with 150 ml EtOAc, and washed with 20 ml distilled water. The organic phase was dried over MgSO4 and concentrated in vacuo and purified by column chromatography (eluting with 1:1 DCM:Hex), to give 4.0 g (95%) of the titled compound.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washwashed with 20 ml
  3. distillationdistilled water
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (eluting with 1:1 DCM:Hex)

Sources & evidence

ORD record
ord-279bed1f5d1b412383ba6ad4818d5018
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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