Water → 6-(4-Morpholinyl)-2-pyridinemethanol

HRID 2183507Notes

Reaction equation

HRID 2183507 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[N:33]=[C:32]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:31]=[CH:30][CH:29]=1)(C(C)(C)C)(C)C.O>C1COCC1>[N:34]1([C:32]2[N:33]=[C:28]([CH2:27][OH:26])[CH:29]=[CH:30][CH:31]=2)[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 224731974-[6-(Tert-butyldimethylsilanyloxymethyl)-pyridin-2-yl]morpholine

Product 1

HCID 224732166-(4-Morpholinyl)-2-pyridinemethanolYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride (1.44 mmol) in THF (1.0 M, 1.44 ml) was added to a stirred solution of 4-[6-(tert-butyldimethylsilanyloxymethyl)-pyridin-2-yl]morpholine (370 mg, 1.2 mmol) in THF (10 ml) at room temperature under N2 and the reaction mixture was stirred at room temperature for 1 h. H2O (30 ml) was added and the organic were extracted with EtOAc (150 ml), then washed with brine (50 ml), dried and concentrated under reduced. The mixture was purified by column chromatography on silica using 100% Et2O as eluent to yield the desired hydroxymethylpyridine (192 mg, 82%). 1H NMR (360 MHz, CDCl3) δ 7.49 (1H, dd, J=8.4, 7.4 Hz), 6.57 (1H, d, J=7.4 Hz), 6.51 (1H, d, J=8.4 Hz), 4.62 (2H, s), 3.83 (4H, t, J=4.9 Hz), 3.50 (4H, t, J=4.9 Hz).

Workup

  1. extractionthe organic were extracted with EtOAc (150 ml)
  2. washwashed with brine (50 ml)
  3. customdried
  4. concentrationconcentrated
  5. customThe mixture was purified by column chromatography on silica using 100% Et2O as eluent

Sources & evidence

ORD record
ord-7dbea7aeb97049f29426dc30322ce781
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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