Dimethyl Carbonate → HCID 21912726, compound

HRID 1245596Notes

Reaction equation

HRID 1245596 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)(=[O:4])[CH2:2][CH3:3].CO[C:20](=[O:23])[O:21][CH3:22].CC(C)([O-])C.[K+]>COC>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][CH:5]([C:1](=[O:4])[CH:2]([CH3:3])[C:20](=[O:23])[O:21][CH3:22])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 21912753tert-Butyl 4-propanoylpiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21912726HCID 21912726, compound

Reagents, catalysts & solvents 1

HCID 8254Dimethyl EtherSolvent

Procedure

A solution of 0.51 g (2.1 mmol) of 4-propionyl-1-(tert-butoxycarbonyl)piperidine (from Step A) and 0.35 mL (17.6 mmol) of dimethylcarbonate in 5 mL of tert-butyl, methylether at 0° C. was treated with 0.45 g (4.0 mmol) of potassium tert-butoxide. After 10 minutes at 0° C., the reaction was stirred at rt for 17 hours and refluxed for 3 hours. The reaction was quenched with 1 N HCl and partitioned between 100 mL of Et2O and 100 mL of 1 N HCl. After separating phases, the organic layer was washed with 100 mL of brine, dried over MgSO4 and concentrated. The residue was purified with a 40M Biotage column using 9:1 v/v of hexanes/acetone as the eluant to afford the title compound as a straw colored oil: RF: 0.32 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.35 (d, J=7.1, 3H), 1.42–1.66 (m, 11H), 1.79–1.80 (m, 2H), 2.68–2.79 (m, 3H), 3.71 (q, J=7.1, 1H), 3.73, 3.77 (2s, 3H), 4.12 (m, 2H).

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe reaction was quenched with 1 N HCl
  3. custompartitioned between 100 mL of Et2O and 100 mL of 1 N HCl
  4. customAfter separating phases
  5. washthe organic layer was washed with 100 mL of brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified with a 40M Biotage column

Sources & evidence

ORD record
ord-27a51560554f413ebd95f6a74981062d
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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