Tris(1,1-dimethylethyl)phosphine → Benzyl 6-(3-(phenylsulfonyl)quinolin-8-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

HRID 2092190Notes

Reaction equation

HRID 2092190 reaction equation
CC(C)([O-])C.[Na+].[C@@H:7]12[CH2:13][NH:12][C@@H:11]1[CH2:10][N:9]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:8]2.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.I[C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[N:46]=[CH:45][C:44]([S:48]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:50])=[O:49])=[CH:43]2>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:51]1([S:48]([C:44]2[CH:45]=[N:46][C:47]3[C:42]([CH:43]=2)=[CH:41][CH:40]=[CH:39][C:38]=3[N:12]2[CH2:13][CH:7]3[CH:11]2[CH2:10][N:9]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:8]3)(=[O:50])=[O:49])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 114067748-Iodo-3-(phenylsulfonyl)quinolineHCID 23635906benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 25196270Benzyl 6-(3-(phenylsulfonyl)quinolin-8-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of sodium t-butoxide (49 mg, 0.51 mmol) and (1S,5S)-benzyl 3,6-diazabicyclo[3.2.0]heptane-3-carboxylate (98 mg, 0.24 mmol) in toluene (3 mL) was stirred under nitrogen. To this was added tri-t-butylphosphine (25 mg, 0.05 mmol), palladium (II) acetate (6.9 mg, 0.03 mmol) and 8-iodo-3-(phenylsulfonyl)quinoline (80 mg, 0.202 mmol). The mixture was then heated at 60° C. for 2 h before partitioning between CH2Cl2 and water. The mixture was filtered through Celite and the organic phase was separated. The water phase was extracted twice with CH2Cl2 and the combined extracts dried (Na2SO4), filtered and concentrated in vacuo to provide the crude material, which was purified by flash chromatography to give the title compound.

Workup

  1. custombefore partitioning between CH2Cl2 and water
  2. filtrationThe mixture was filtered through Celite
  3. customthe organic phase was separated
  4. extractionThe water phase was extracted twice with CH2Cl2
  5. dry with materialthe combined extracts dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide the crude material, which
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-9c7fb832eebb45c1a828443bceb61da8
Source dataset
uspto-grants-2013_05
Patent number
US08440694B2

Reaction notes

Loading…