Aluminium lithium hydride → Methyl-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}amine

HRID 272879Notes

Reaction equation

HRID 272879 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12](=O)[N:13](C)[CH2:14][C:15]1([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:23][CH:22]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)(C)(C)C>C1COCC1>[CH3:12][NH:13][CH2:14][C:15]1([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:23][CH:22]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68576319HCID 68576319, compound

Product 1

HCID 11674363Methyl-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}amineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of LiAlH4 (2.59 g, 68.18 mmol) in dry THF at 0° C. was added dropwise a solution of methyl-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}carbamic acid tert-butyl ester (9.50 g, 22.72 mmol). The reaction mixture was then brought to room temperature and finally heated to reflux for 3 h. The reaction mixture was quenched with aqueous NaOH solution and filtered over a short pad of celite, dried over Na2SO4 and concentrated under reduced pressure to provide the title compound (7.1 g, 94% yield). 1H NMR (400 MHz, CDCl3) δ 1.71-1.78 (m, 4H); 1.80-1.90 (m, 2H); 1.88-2.02 (m, 2H); 2.06-2.14 (m, 2H); 2.23 (s, 3H); 2.46-2.53 (m, 4H); 2.51-2.63 (m, 4H); 3.47-3.56 (m, 2H); 3.70-3.77 (m, 2H); 3.99 (t, 2H); 6.86 (d, 2H); 7.17 (d, 2H).

Workup

  1. customwas then brought to room temperature
  2. temperaturefinally heated
  3. temperatureto reflux for 3 h
  4. customThe reaction mixture was quenched with aqueous NaOH solution
  5. filtrationfiltered over a short pad of celite
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-516bb57f215544358d56282b3d669815
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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