Aluminium lithium hydride → Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamate
Reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[C:13]([C:15](OCC)=[O:16])[CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:16][CH2:15][C:13]1[N:14]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH:10]=[CH:11][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of ethyl 6-(bis(tert-butoxycarbonyl)amino)picolinate 77 (11.0 g, 33 mmol) in THF (120 mL) under nitrogen was added LiAlH4 (3.80 g, 100 mmol) in THF (60 mL) over a period of 30 min at 0° C. The reaction mixture was stirred at 0° C. for 6 h and carefully quenched by the addition of H2O (2.0 mL) and 10% NaOH solution (4.0 mL) at 0° C. The reaction mixture was filtered and the filtrate was dried (Na2SO4) and concentrated under reduced pressure. The resulting residue purified by chromatography (1:1 petroleum ether:ethyl acetate) to afford 78 (3.0 g, 41% yield).
Workup
- customcarefully quenched by the addition of H2O (2.0 mL) and 10% NaOH solution (4.0 mL) at 0° C
- filtrationThe reaction mixture was filtered
- dry with materialthe filtrate was dried (Na2SO4)
- concentrationconcentrated under reduced pressure
- customThe resulting residue purified by chromatography (1:1 petroleum ether:ethyl acetate)
Sources & evidence
- ORD record
- ord-411ebd6ee3bd46548d1f22c9cf550f17
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09326986B2
Reaction notes
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