Ammonium Chloride → HCID 70982984, compound

HRID 339083Notes

Reaction equation

HRID 339083 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([CH3:25])=[N:22]2)=[CH:17][CH:16]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[CH3:25][C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][C:15]([O:14][C@@H:10]3[CH2:11][CH2:12][CH2:13][C@H:9]3[OH:8])=[CH:16][CH:17]=2)[N:22]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 86707556HCID 86707556, compound

Product 1

HCID 70982984HCID 70982984, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of crude trans-7-((2-((tert-butyldimethylsilyl)oxy)cyclopentyl)oxy)-2-methylquinoline (3.0 g, 8.4 mmol) in THF (10 mL) was added 1.0 M TBAF in THF (17 mL, 17 mmol). After stirring at ambient temperature for 1 hour, saturated aqueous NH4Cl was added to the reaction mixture. The mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by flash chromatography on silica gel (2% MeOH in EtOAc) to give trans-2-((2-methylquinolin-7-yl)oxy)cyclopentanol (0.065 g, 3% for two steps).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (2% MeOH in EtOAc)

Sources & evidence

ORD record
ord-c9c81e6dcc0b4de4a53f7a8b4a1a831e
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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