Piperidine → HCID 69066473, compound

HRID 1819524Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH2:10][C@H:9]1[C:31](=[O:47])[NH:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]2=[O:45])=[CH:35][C:34]=1[F:46])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:31](=[O:47])[NH:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]2=[O:45])=[CH:35][C:34]=1[F:46])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

(2S,4S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (160 mg) was dissolved in CH2Cl2 (2 ml) and piperidine (43 μl) was added. The mixture was stirred for 17 h at 25° C. The crude product was purified by chromatography (silica gel; gradient: CH2Cl2->methanol 2N NH3) to yield (2S,4S)-4-amino-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as colorless amorphous solid (96 mg). MH+=417.5

Workup

customThe crude product was purified by chromatography (silica gel; gradient: CH2Cl2->methanol 2N NH3)

Sources & evidence

ORD record: ord-f4a5fa677e144d97aa8dc21ab95d3463
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601752B2

Reaction notes

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