Water → 1-tert-Butyl 2-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate

HRID 2185424Notes

Reaction equation

[C-:1]#[N:2].[Na+].[CH3:4][O:5][C:6](=[O:30])[C@@H:7]1[CH2:11][C@H:10](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9][N:8]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].O>CN(C)C=O>[CH3:4][O:5][C:6](=[O:30])[C@@H:7]1[CH2:11][C@@H:10]([C:1]#[N:2])[CH2:9][N:8]1[C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24]

Participants

Conditions

Temperature: 65 °C

Procedure

Sodium cyanide (245 mg) was added to a stirred solution of N-tert-butoxycarbonyl-cis-4-p-toluenesulfonyloxy-L-proline methyl ester (Compound D101 (K), 1.00 g) in N,N-dimethylformamide (10 mL)-water (22 mL). After stirring at 65° C. for 16 hr, the solvents were removed in vacuo. The residue was diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:toluene=1:20, v/v) to give the title compound (197 mg): 1H NMR (400 MHz, CDCl3) δ 1.40 (s, 9H), 2.33-2.52 (m, 2H), 3.25 (m, 1H), 3.69 (m, 1H), 3.75 (s, 3H), 3.90 (m, 1H), and 4.37-4.49 (m, 1H).

Workup

customthe solvents were removed in vacuo
additionThe residue was diluted with ethyl acetate
washwashed with water and brine
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record: ord-53c76180ec224c96be8564d89cfcfcf9
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399629B1

Reaction notes

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