Pyridine → HCID 54718313, compound

HRID 2213538Notes

Reaction equation

HRID 2213538 reaction equation
[C:1]12([O:11][CH2:12][C:13](O)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:28][C:29]1([CH3:37])[O:34][C:33](=[O:35])[CH2:32][C:31](=[O:36])[O:30]1.N1C=CC=CC=1>C(Cl)Cl>[C:1]12([O:11][CH2:12][C:13](=[C:32]3[C:33](=[O:35])[O:34][C:29]([CH3:37])([CH3:28])[O:30][C:31]3=[O:36])[OH:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 682631,1'-CarbonyldiimidazoleHCID 6484207AKOS BB-8750

Product 1

HCID 54718313HCID 54718313, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (adamantan-1-yloxy)-acetic acid (32.3 g, 153 mmol) and 1,1′-carbonyl-diimidazole (27.6 g, 170 mmol) in DCM (600 mL) was stirred at 0° C. for 15 minutes, then at room temperature for 75 minutes. The mixture was concentrated in vacuo (˜300 mL) and the solution was then added dropwise, over 20 minutes, to a solution of 2,2-dimethyl-1,3-dioxan-4,6-dione (22.1 g, 153 mmol) and pyridine (30 mL, 371 mmol) in DCM (450 mL) at 0° C. under argon. The mixture was allowed to warm to room temperature and stirred for 16 hours. The organic solution was washed with 2N HCl (2×500 mL), brine (500 mL) and dried (MgSO4). The filtrate was evaporated and the residue triturated with hexane to give the title compound as a white solid (50.1 g, 97%). 1H NMR (CDCl3) 4.91 (2H, s), 2.18 (3H, br s), 1.81-1.81 (6H, m), 1.73 (6H, s), 1.68-1.58 (6H, m).

Workup

  1. concentrationThe mixture was concentrated in vacuo (˜300 mL)
  2. washThe organic solution was washed with 2N HCl (2×500 mL), brine (500 mL)
  3. dry with materialdried (MgSO4)
  4. customThe filtrate was evaporated
  5. customthe residue triturated with hexane

Sources & evidence

ORD record
ord-95e94f3ab7704fc88630fbc655955561
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

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