HCID 68772476, compound → HCID 68768813, compound

HRID 2265195Notes

Reaction equation

HRID 2265195 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]2[C:9]=1[C:10](=[O:28])[N:11]([CH2:19][C@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21])[C:12]2=[O:18])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][C:8]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]2[C:9]=1[C:10](=[O:28])[N:11]([CH2:19][C@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21])[C:12]2=[O:18]

Participants

4

Reactant 1

HCID 68772476HCID 68772476, compound

Product 1

HCID 68768813HCID 68768813, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-[6-Bromo-1,3-dioxo-2-(2-phenyl-propyl)-2,3-dihydro-1H-isoindol-4-yl]-carbamic acid tert-butyl ester (160 mg, 0.35 mmol) was stirred in a mixture of DCM (2 mL) and TFA (1 mL) for 3 h at rt. The mixture was concentrated, and the residue was diluted with satd. aq. NaHCO3 and extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to give a yellow oil. Purification by flash chromatography (EtOAc/hexanes) gave 110 mg (87%) of the desired amine as a yellow foam. 1H NMR (500 MHz, CDCl3): 7.31-7.23 (m, 4H), 7.22-7.17 (m, 2H), 6.81 (d, J=1.5, 1H), 5.19 (br s, 2H), 3.78 (dd, J=13.6, 7.6, 1H), 3.71 (dd, J=13.6, 8.2, 1H), 3.30 (app sextet, Japp=7.5, 1H), 1.29 (d, J=7.0, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with satd
  3. extractionaq. NaHCO3 and extracted with DCM (3×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-9f191504defa42a488bee0fd0da1c500
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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