Hydrochloric Acid → tert-Butyl-(4R)-4-(3-iodo-4-chlorophenyl)-2-oxopyrrolidinecarboxylate

HRID 1799210Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11][C:10](=[O:13])[CH2:9]2)=[CH:4][C:3]=1[I:14].C(N(CC)CC)C.[C:22](=O)([O:28]C(C)(C)C)[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:24]([O:23][C:22]([N:11]1[CH2:12][C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([I:14])[CH:4]=2)[CH2:9][C:10]1=[O:13])=[O:28])([CH3:27])([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To (4R)-4-(4-chloro-3-iodophenyl)pyrrolidin-2-one (17.4 g, 54.4 mmol) was added 50 mL DCM. The solution was cooled to 0° C. Triethylamine (9.1 mL, 65.25 mmol) was added followed by di-tert butyl carbonate (13.1 g, 59.04 mmol) in 60 mL of DCM. A catalytic amount of DMAP was added, the mixture warmed to room temperature, and then stirred overnight at room temperature. A 5% solution of HCl (50 mL) was added and the organic phase separated. The DCM layers were then washed with brine and evaporated to give the title compound (43a) as a yellowish solid (18.3 g, 80% yield). 1H-NMR (400 MHz, CD3OD): δ 7.83-7.84 d, J=2 Hz, 1H), 7.35-7.46 (m, 1H), 7.31-7.33 (m, 1H), 4.11-4.15 (m, 1H), 3.62-3.67 (m, 2H), 3.45-3.61 (m, 1H), 2.80-2.84 (m, 1H), 2.69-2.74 (m, 1H) 1.52 (s, 9H); MS (ESI) m/z 443.86 (M+Na)+.

Workup

temperaturethe mixture warmed to room temperature
customthe organic phase separated
washThe DCM layers were then washed with brine
customevaporated

Sources & evidence

ORD record: ord-cb6465344cb047c9913f95a3fbc2eac9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344028B2

Reaction notes

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