Diisopropylethylamine → HCID 68434290, compound

HRID 1867380Notes

Reaction equation

HRID 1867380 reaction equation
Cl.[OH:2][CH2:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O.CCN(C(C)C)C(C)C>CCOC(C)=O.CN(C=O)C>[C:15]([O:14][C:12]([N:5]1[CH2:6][CH2:7][CH2:8][CH:9]([OH:10])[CH:4]1[CH2:3][OH:2])=[O:11])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 30841853-Hydroxy-2-(hydroxymethyl)pyridine hydrochloride

Product 1

HCID 68434290HCID 68434290, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 5 g (31.00 mmol) of 2-hydroxymethyl-pyridin-3-ol hydrochlorid and 2.50 g 5% Rh/Alox in 100 ml AcOEt was stirred under hydrogen atmosphere 20 h at 25° C. and 8 bar. The suspension was filtered and evaporated to give an yellow oil. The crude product was treated with 8.78 g (40.00 mmol) BOC2O and 12 ml (93.00 mmol) Hunig's base in 30 ml DMF under ice cooling for 25 h. An extraction (water/brine/AcOEt) and two crystallizations (AcOEt, MeCN/CH2Cl2) gave 1.77 g (25%) of the title compound as a white solid. MS: 232.0 (MH+).

Workup

  1. filtrationThe suspension was filtered
  2. customevaporated
  3. customto give an yellow oil
  4. extractionAn extraction (water/brine/AcOEt) and two crystallizations (AcOEt, MeCN/CH2Cl2)

Sources & evidence

ORD record
ord-187e74965ded44cd8566f69c52fe22ad
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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