Aluminium lithium hydride → 2-(Boc-amino)-4-(hydroxymethyl)pyridine

HRID 1789794Notes

Reaction equation

HRID 1789794 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:6]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:15]([O:14][C:12](=[O:13])[NH:11][C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[CH:9][N:8]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54428289HCID 54428289, compound

Product 1

HCID 231510012-(Boc-amino)-4-(hydroxymethyl)pyridineYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of to 2-[N,N-bis(tert-Butoxycarbonyl)amino]-isonicotinic acid ethyl ester (35.0 g, 95.5 mmol) in THF (350 mL) was treated with LiAlH4 (7.25 g, 191 mmol) and refluxed for 1 h under nitrogen. The reaction mixture was poured carefully onto crushed ice and the product extracted several times with CHCl3 and CHCl3: MeOH (9:1). The combined organic extracts were dried, filtered and concentrated under reduced pressure to give (4-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (18.5 g, 86%) as a pale yellow solid.

Workup

  1. temperaturerefluxed for 1 h under nitrogen
  2. additionThe reaction mixture was poured carefully
  3. customonto crushed ice
  4. extractionthe product extracted several times with CHCl3 and CHCl3: MeOH (9:1)
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e22be225eb1c4553a6fd980d9b34a803
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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