Hydroxyamine hydrochloride → tert-butyl (1R,3S,4S,6E)-3-[(2S)-2-cyanopyrrolidine-1-carbonyl]-6-hydroxyimino-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 456759Notes

Reaction equation

HRID 456759 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:13](=O)[CH2:14]2)[N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:9])#[N:2].Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+]>C(O)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:13](=[N:26]/[OH:27])/[CH2:14]2)[N:11]1[C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[O:9])#[N:2]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86598907tert-Butyl (1R,3S,4S)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 145785765tert-butyl (1R,3S,4S,6E)-3-[(2S)-2-cyanopyrrolidine-1-carbonyl]-6-hydroxyimino-2-azabicyclo[2.2.1]heptane-2-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (1R,3S,4S)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 22-1 (296 mg) in ethanol (5 mL) and water (1 mL),were added hydroxylamine hydrochloride (123 mg) and sodium acetate (153 mg). The mixture was stirred at 80° C. for 20 minutes.

Sources & evidence

ORD record
ord-ac2a8ff429ed4b26a185ddbb10bb8372
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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