1,1'-Carbonyldiimidazole → [1-(Imidazole-1-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

HRID 406460Notes

Reaction equation

[CH:1]1[N:5]=[CH:4][N:3]([C:6](N2C=NC=C2)=[O:7])[CH:2]=1.[C:13]([O:17][C:18](=[O:25])[NH:19][CH:20]1[CH2:24][CH2:23][NH:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14]>C1COCC1.C(Cl)Cl>[C:13]([O:17][C:18](=[O:25])[NH:19][CH:20]1[CH2:24][CH2:23][N:22]([C:6]([N:3]2[CH:2]=[CH:1][N:5]=[CH:4]2)=[O:7])[CH2:21]1)([CH3:16])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 57.5 °C

Procedure

To a suspension of CDI (3.8 g, 20.5 mmol) in THF (40 mL) was added pyrrolidin-3-yl-carbamic acid tert-butyl ester (3.99 g, 20.5 mmol) and the reaction mixture was heated at about 55-60° C. for about 4 h. The reaction mixture was cooled at ambient temperature and concentrated in vacuo to afford an yellow oil. The residue was dissolved in DCM (40 mL), washed with water (2×30 mL), and the organic portion was separated, dried over MgSO4, filtered, and concentrated in vacuo to give [1-(imidazole-1-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (5.06 g, 88%) as a yellow oil which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 2.08 min; m/z: (M+H)+ 281.

Workup

temperatureThe reaction mixture was cooled at ambient temperature
concentrationconcentrated in vacuo
customto afford an yellow oil
washwashed with water (2×30 mL)
customthe organic portion was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5d710994e2494e398c15169d947af936
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754107B2

Reaction notes

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