Tetrabutylammonium Fluoride → 4-(2-Cyclopropylindol-1-yl)cyclohexanol

HRID 1092418Notes

Reaction equation

HRID 1092418 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH:24]2[CH2:26][CH2:25]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:24]1([C:16]2[N:15]([CH:12]3[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH2:11]3)[C:23]3[C:18]([CH:17]=2)=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 576757611-[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole

Product 1

HCID 576757584-(2-Cyclopropylindol-1-yl)cyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 1-[4-(tert-butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole from above (10.4 mmol) was dissolved in tetrahydrofuran (150 mL), and tetrabutylammonium fluoride (21 mL, 1 M in THF, 21 mmol) was added. After the reaction was stirred for 72 hours it was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was dried (MgSO4), concentrated and purified by SiO2 chromatography (10-50% ethyl acetate/hexanes) to give two (cis/trans) isomers (355 mg of the more polar isomer, 681 mg of the less polar isomer) of the desired alcohol. LC-MS (C17H21NO calc'd 255) m/z 256 (M+H).

Workup

  1. concentrationwas concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography (10-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dceffded7f8246fea9a9f201c4b9b2f8
Source dataset
uspto-grants-2012_03
Patent number
US08129424B2

Reaction notes

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