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

HRID 1363227Notes

Reaction equation

HRID 1363227 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]([F:36])([F:35])[C:21]([NH:23][C@H:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:27]([OH:34])[CH2:26][CH2:25]1)=[O:22].N1C=CN=C1>CN(C=O)C.CCOC(C)=O>[Si:5]([O:34][C@H:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:24]([NH:23][C:21](=[O:22])[C:20]([F:35])([F:36])[F:19])[CH2:25][CH2:26]1)([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 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 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butylchlorodiphenylsilane (4.4 mL) was added to a stirred solution of 2,2,2-trifluoro-N-((1R,4R)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (2.2 g) and imidazole (1.7 g) in DMF (35 mL). The reaction mixture was stirred at room temp overnight. The reaction mixture was diluted with EtOAc (150 mL), and washed with distilled water (20 mL). 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. 1H-NMR (300 MHz, CDCl3) □ 7.7 (d, 2H), 7.6 (d, 2H), 7.4 (m, 6H), 7.2 (m, 4H), 6.3 (broad s, 1H), 5.2 (q, 1H), 4.8 (t, 1H), 2.4 (m, 1H), 1.8 (m, 2H), 1.6 (m, 1H) ppm.

Workup

  1. washwashed with distilled water (20 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (eluting with 1:1 DCM/Hex)

Sources & evidence

ORD record
ord-a1da1ea9dec2493090b838a9c4cb62a7
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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