Water → 1-[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-yl]methanamine

HRID 273034Notes

Reaction equation

HRID 273034 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH2:21][NH2:22])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 685766664-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 685780131-[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-yl]methanamineYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile (3.5 g, 11 mmol) in THF (35 ml) at 0° C. was added dropwise lithium aluminium hydride (1M solution in ether, 44 ml, 44 mmol). The reaction was allowed to warm up to room temperature and stirred for 4 hours until complete. The reaction mixture was cooled to 0° C., water (1.66 mL) was added followed by NaOH (2.0M, 1.66 mL) and water (4.97 mL). The mixture was filtered through a short pad of celite, eluting with dichloromethane:methanol (97:3, 150 ml) and concentrated in vacuo. Solid obtained was partitioned between ethyl acetate (50 ml) and sodium bicarbonate (50 ml). The organic layer was then dried over sodium sulphate, filtered and concentrated in vacuo to give the title compound (2.04 g, 58%). LRMS APCI+ m/z 322 [MH]+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationThe mixture was filtered through a short pad of celite
  3. washeluting with dichloromethane:methanol (97:3, 150 ml)
  4. concentrationconcentrated in vacuo
  5. customSolid obtained
  6. customwas partitioned between ethyl acetate (50 ml) and sodium bicarbonate (50 ml)
  7. dry with materialThe organic layer was then dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cac14f8be1e4c9c8ecc01bcfa76eb29
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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