(6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-one → (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 851398Notes

Reaction equation

HRID 851398 reaction equation
CNN(CCC)NC.[CH3:9][C:10]1([CH3:30])[O:17][CH2:16][CH2:15][C@H:14]2[N:11]1[C:12](=[O:29])[C@@H:13]2[N:18]1C(=O)C2=CC=CC=C2C1=O>CO.ClCCl>[NH2:18][C@H:13]1[C:12](=[O:29])[N:11]2[C@@H:14]1[CH2:15][CH2:16][O:17][C:10]2([CH3:30])[CH3:9]

Participants

5

Reactant 2

HCID 53799173(6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-oneHCID 56982963N,N-dimethylaminopropylamine

Product 1

HCID 12804734(6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-oneYield 59.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethylaminopropylamine (91 μl) was added to a solution of (6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-one (80 mg) in a mixture of methanol (1.4 ml) and dichloromethane (0.7 ml) at 0° C. under a nitrogen atmosphere. The solution was stirred at the same temperature for two hours and left at ambient temperature for 24 hours. The mixture was evaporated and the residue was chromatographed on silica gel (1.5 g; eluting with 3 to 5% methanol in dichloromethane) to give 27 mg (59.5%) of (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one: IR (CH2Cl2): 3100-3600 (broad) and 1735 cm-1 ; NMR (CDCl3) δ: 1.41 (s, 3H), 1.72 (s, 3H), 1.5-2.1 (m, 4H), 3.34 (ddd, J=2, 5 and 10 Hz, 1H), and 3.7-3.9 (m, 3H)

Workup

  1. waitleft at ambient temperature for 24 hours
  2. customThe mixture was evaporated
  3. customthe residue was chromatographed on silica gel (1.5 g; eluting with 3 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-eecb9ba011ef47519f1dd06136e10897
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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