Pyrrolidine → HCID 86598897, compound

HRID 456747Notes

Reaction equation

[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13](OS(C)(=O)=O)[CH2:14]2)[N:11]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:9])#[N:2].[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C)C=O>[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:14]2)[N:11]1[C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[O:9])#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-[(methylsulfonyl) oxy]-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 12-1 (153 mg) in dimethylformamide (2.0 mL), was added pyrrolidine (79 mg). The mixture was stirred at 80° C. for 1 hr. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with chloroform and methanol (19:1) to give the target compound (91 mg).

Workup

customThe resulting mixture was evaporated in vacuo
customthe residue was chromatographed on silica gel eluting with chloroform and methanol (19:1)

Sources & evidence

ORD record: ord-6de8f5383ab44c1a98e0f59d4f82f89f
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186731B2

Reaction notes

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