Ammonium Chloride → tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

HRID 1789803Notes

Reaction equation

HRID 1789803 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:7][CH:6]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1>[C:15]([O:14][C:12](=[O:13])[NH:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][OH:3])=[CH:6][N:7]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 21879719Ethyl 6-(((tert-butoxy)carbonyl)amino)pyridine-3-carboxylate

Product 1

HCID 3575389tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamateYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 6-tert-butoxycarbonylamino-nicotinic acid ethyl ester (3.50 g, 13.1 mmol) in THF (20 mL) under nitrogen was added LiAlH4 (0.91 g, 24.0 mmol) in THF (20 mL) over a period of 2 h. The reaction mixture was stirred for 6 h, then NH4Cl (sat.) was added (carefully) until neutral solution. The mixture was filtered and concentrated under reduced pressure to give (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (2.00 g 68%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-974d6f3d98044b19b9a4be784b331090
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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