Tetrabutylammonium Fluoride → HCID 68502906, compound

HRID 876358Notes

Reaction equation

HRID 876358 reaction equation
[Si]([O:8][CH:9]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][C:11]2[CH:17]=[C:18]([C:21]3[N:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:19]=[CH:20][C:10]1=2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:16][N:13]1[CH2:14][CH2:15][CH:9]([OH:8])[C:10]2[CH:20]=[CH:19][C:18]([C:21]3[N:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][C:11]=2[CH2:12]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68504302HCID 68504302, compound

Product 1

HCID 68502906HCID 68502906, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of the (−)-5-(tert-butyldimethylsilyloxy)-2-methyl-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine (2.14 g, 5.8 mmol) from Step G above in THF was added TBAF (1.0 M in THF, 10 mL, 10 mmol). The reaction mixture was stirred at room temperature for 3 hours. The solvent was removed. The residue was purified by flash chromatography (97:2.7:0.3 to 93:6.3:0.7 ethyl acetate/methanol/concentrated ammonium hydroxide) to give (−)-2-methyl-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-ol (1.34 g, 90%) as a white solid ([α]25D, −28.6°, (C, 0.18 Methanol)): ESI MS m/z 256 [M+H]+.

Workup

  1. customThe solvent was removed
  2. customThe residue was purified by flash chromatography (97:2.7:0.3 to 93:6.3:0.7 ethyl acetate/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-90632fe801f04e9695c98fa736ddbd66
Source dataset
uspto-grants-2015_03
Patent number
US08987252B2

Reaction notes

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