Triethylamine → HCID 66744440, compound

HRID 1959425Notes

Reaction equation

[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(N(CC)CC)C.[CH:21]1[N:25]=[CH:24][N:23]([C:26](N2C=NC=C2)=[O:27])[CH:22]=1>C1COCC1.CCOC(C)=O>[N:23]1([C:26]([O:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)=[O:27])[CH:22]=[CH:21][N:25]=[CH:24]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate (360 mg, 1.9 mmol) in THF (8 mL) was added triethylamine (253 mg, 349 μL, 2.5 mmol) followed by the addition of CDI (374 mg, 2.3 mmol) portionwise. The reaction mixture was heated at 50° C. for 3 h, cooled to room temperature and diluted with EtOAc. The organic layer was washed with 1 M HCl solution, dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified via silica gel column chromatography using 20 to 100% EtOAc in hexanes to obtain (S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl 1H-imidazole-1-carboxylate (345 mg, 64%). 1HNMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 7.42 (d, J=1.2 Hz, 1H), 7.09 (s, 1H), 4.46 (s, 1H), 3.66 (dd, J=33.8, 10.7 Hz, 1H), 3.56-3.29 (m, 2H), 2.25 (s, 1H), 2.04-1.87 (m, 2H), 1.48 (t, J=4.0 Hz, 9H). LC/MS m/z 282.4 [M+H]+.

Workup

temperaturecooled to room temperature
washThe organic layer was washed with 1 M HCl solution
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record: ord-6a824b33d5c045de9950c8c74d3dbb83
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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