Water → tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

HRID 520495Notes

Reaction equation

HRID 520495 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[OH:14][CH2:13][C:12]1[CH:18]=[CH:19][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66694548HCID 66694548, compound

Product 1

HCID 3575389tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamateYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of ethyl 6-(bis(tert-butoxycarbonyl)amino)nicotinate 115 (300 g, 819 mmol) in THF (1.2 L) was added LiAlH4 (57.6 g, 1.51 mol) in THF (3 L) over a period of 30 min at 0° C. The reaction mixture was stirred for 6 h, and H2O (30.0 ml) and 10% NaOH solution (60.0 mL) were added. The solids were removed by filtration and the filtrate was dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (CH2Cl2; MeOH=40:1) to give 116 (85.0 g, 46% yield).

Workup

  1. customThe solids were removed by filtration
  2. dry with materialthe filtrate was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography (CH2Cl2; MeOH=40:1)

Sources & evidence

ORD record
ord-3e6c0bd8cd5047f28ca12844bc91e6f5
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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