Cyclohexane → 3-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxane-5-carbonyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 83051Notes

Reaction equation

HRID 83051 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.C1CCC(N=C=NC2CCCCC2)CC1.[C:26]([O:30][C:31]([N:33]1[CH2:36][CH:35]([C:37](O)=[O:38])[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C1CCCCC1>CN(C1C=CN=CC=1)C.ClCCl>[C:26]([O:30][C:31]([N:33]1[CH2:36][CH:35]([C:37]([CH:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])=[O:38])[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 8078CyclohexaneHCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

HCID 671548113-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxane-5-carbonyl)-azetidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Meldrum's acid (0.85 g, 5.97 mmol), DCC (1.22 g, 5.97 mmol), and DMAP (1.45 g, 11.94 mmol) were successively added to a solution of azetidine-1,3-dicarboxylic acid mono-tert-butyl ester (1.2 g, 5.97 mmol) in dichloromethane (25 mL) at room temperature. The reaction mixture was stirred overnight and then diluted by addition of cyclohexane (25 mL). The precipitate of dicyclohexyl urea was then filtered and rinsed with diethyl ether (100 mL). The mother liquors were diluted with DCM (100 mL) and washed with a 1M solution of aqueous HCl (2×30 mL), dried over sodium sulfate, filtered and concentrated to dryness. After trituration in diethyl ether the title compound was obtained as a white solid (1.9 g, 100%).

Workup

  1. filtrationThe precipitate of dicyclohexyl urea was then filtered
  2. washrinsed with diethyl ether (100 mL)
  3. additionThe mother liquors were diluted with DCM (100 mL)
  4. washwashed with a 1M solution of aqueous HCl (2×30 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9525a9c43ae545a2be36e857be7c1265
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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