HCID 68817291, compound → HCID 68817298, compound

HRID 736821Notes

Reaction equation

HRID 736821 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[C:24](=[O:25])[C@:23]3([CH3:26])[C@H:19]2[CH2:20][CH2:21][CH2:22]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[C:24](=[O:25])[C@:23]3([CH3:26])[C@H:19]2[CH2:20][CH2:21][CH2:22]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 68817291HCID 68817291, compound

Product 1

HCID 68817298HCID 68817298, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

According to the procedure of Example 47, Step 6, using (1S,5R)-6-{[4-(benzyloxy)phenyl]sulfonyl}-1-methyl-6-azabicyclo[3.2.0]heptan-7-one (354 mg, 0.954 mmol) and catalytic 10% Pd/C, with ethyl acetate added to aid solubility, (1S,5R)-6-[(4-hydroxyphenyl)sulfonyl]-1-methyl-6-azabicyclo[3.2.0]heptan-7-one was obtained (291 mg, 100%) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.24-1.35 (m, 4H) 1.46-1.56 (m, 1H) 1.75 (dt, J=12.32, 6.09 Hz, 1H) 2.02 (dd, J=12.63, 5.56 Hz, 1H) 2.07-2.16 (m, 1H) 4.09 (d, J=4.04 Hz, 1H) 6.93 (s, 1H) 6.97 (d, J=8.84 Hz, 2H) 7.81 (d, J=8.84 Hz, 2H).

Sources & evidence

ORD record
ord-c14b0c6f568845bb9ca6a38b3cb22337
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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