Ethyl 6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate → Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamate

HRID 85149Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][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]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl 6-(tert-butoxycarbonylamino)picolinate (92; 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 water (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 tert-butyl 6-(hydroxymethyl)pyridin-2-ylcarbamate 93 (3.0 g, 41%).

Workup

customcarefully quenched by the addition of water (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-21fa720609b14fd18a8090f1cfade985
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846947B2

Reaction notes

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