Lithium diisopropylamide → HCID 22992262, compound

HRID 1060634Notes

Reaction equation

HRID 1060634 reaction equation
[NH2:1][CH:2]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[CH2:3][CH:4]1[CH2:8][CH2:7][O:6][CH2:5]1.CS(OC1CCOCC1)(=O)=O.[Li+].CC([N-]C(C)C)C>>[NH2:1][CH:2]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[CH:3]1[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11344352Oxan-4-yl methanesulfonateHCID 22992279219660-75-02×

Product 1

HCID 22992262HCID 22992262, compound

Procedure

The methaneamine derivative was synthesized essentially according to the procedure described for the synthesis of 1-amino-1-(3-pyridyl)-2-(3-tetrahydrofuranyl)-ethane. Thus, tetrahydropyran-4-ol methane sulfonate (0.99 g, 5.5 mmol), prepared according to the procedure of Suto et al., J. Med. Chem., 34:2484 (1991), was treated with the imine anion generated by reacting N-(diphenylmethylidene)-3-(aminomethyl)pyridine (1.36 g, 5.0 mmol) with LDA (5.5 mmol in 5.0 mL tetrahydrofuran). A work up similar to the one described for the synthesis of 1-amino-1-(3-pyridyl)-2-(3-tetrahydrofuranyl)-ethane, followed by purification by column chromatography (15% methanol in chloroform) yielded 1-amino-1-(3-pyridyl)-1-(4-tetrahydropyranyl)-methane (499 mg) in 52% yield.

Workup

  1. customThe methaneamine derivative was synthesized essentially
  2. customfollowed by purification by column chromatography (15% methanol in chloroform)

Sources & evidence

ORD record
ord-a8499f68717f4aa9b1a54a74ea418376
Source dataset
uspto-grants-2003_02
Patent number
US06525065B1

Reaction notes

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