(2R)-3-aminopropane-1,2-diol → 3-(t-Butoxycarbonyl)-6-[(r)-propane-1,2-diol-3-yl]aminopyridine

HRID 412500Notes

Reaction equation

HRID 412500 reaction equation
Cl[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][N:3]=1.[NH2:15][CH2:16][C@@H:17]([OH:20])[CH2:18][OH:19]>C(O)(C)C>[C:9]([O:8][C:6]([C:5]1[CH:4]=[N:3][C:2]([NH:15][CH2:16][C@@H:17]([OH:20])[CH2:18][OH:19])=[CH:14][CH:13]=1)=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 6994409(2R)-3-aminopropane-1,2-diolHCID 11521348Tert-butyl 6-chloropyridine-3-carboxylate

Product 1

HCID 229773083-(t-Butoxycarbonyl)-6-[(r)-propane-1,2-diol-3-yl]aminopyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of t-butyl 6-chloronicotinate (4.69 g, 0.0220 mol) and (R)-3-amino-1,2-propanediol (5.00 g, 0.0549 mol) in isopropanol (20 ml) was heated at 100° C. overnight. Solvent was removed under vacuum, and the residue taken up in ethyl acetate, washed with water, brine, dried (MgSO4), and evaporated to give nearly pure product as a yellow oil. Yield 5.90 g (99%). 1H NMR. MS: 269 [M+H]+.

Workup

  1. customSolvent was removed under vacuum
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give nearly pure product as a yellow oil

Sources & evidence

ORD record
ord-6a627c9c650e4f2387ae8c940aad686f
Source dataset
uspto-grants-2003_05
Patent number
US06562844B2

Reaction notes

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