Aluminium lithium hydride → tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

HRID 85154Notes

Reaction equation

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

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl 6-(tert-butoxycarbonylamino)nicotinate (100; 10.0 g, 27.3 mmol) in THF (40 mL) was added LiAlH4 (1.92 g, 50.5 mmol) in THF (60 mL) over a period of 30 min at 0° C. The resulting reaction mixture was stirred at 0° C. for 6 h. The reaction was then quenched by carefully adding water (1.0 ml) and 10% NaOH solution (2.0 mL) at 0° C. The resulting mixture was filtered and the filtrate was dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (dichloromethane:methanol=40:1) to afford tert-butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate 101 (4.50 g, 74%).

Workup

customThe resulting reaction mixture
customThe reaction was then quenched by carefully adding water (1.0 ml) and 10% NaOH solution (2.0 mL) at 0° C
filtrationThe resulting mixture was filtered
dry with materialthe filtrate was dried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by chromatography (dichloromethane:methanol=40:1)

Sources & evidence

ORD record: ord-e18cd82c18df4e94943c69918c7a8fb9
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846947B2

Reaction notes

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