Aluminium lithium hydride → tert-butyl N-[6-(hydroxymethyl)pyridin-3-yl]carbamate

HRID 85162Notes

Reaction equation

HRID 85162 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](OCC)=[O:16])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[OH:16][CH2:15][C:12]1[N:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 671700275-tert-Butoxycarbonylamino-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 40151875tert-butyl N-[6-(hydroxymethyl)pyridin-3-yl]carbamateYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ethyl 5-(tert-butoxycarbonylamino)picolinate (112; 8.9 g, 24.0 mmol) in ethyl ether (200 mL) was added LiAlH4 (1.80 g, 48 mmol) in ethyl ether (100 mL) over a period of 30 min at 0° C. The resulting reaction mixture was stirred at 0° C. for 3 h and then carefully quenched by carefully adding water (1.0 mL) and 10% NaOH solution (2.0 mL). The mixture was filtered; the filtrate was dried (Na2SO4) and concentrated under reduced pressure to afford tert-butyl 6-(hydroxymethyl)pyridin-3-ylcarbamate 113 (4.20 g, 78%).

Workup

  1. customThe resulting reaction mixture
  2. customcarefully quenched by carefully adding water (1.0 mL) and 10% NaOH solution (2.0 mL)
  3. filtrationThe mixture was filtered
  4. dry with materialthe filtrate was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f255c1a7310e4ed792e6b0b887833bff
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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