Toluene → HCID 68733649, compound

HRID 387518Notes

Reaction equation

HRID 387518 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([C@@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(C(C)C)C(C)C.CO[CH:42]1[N:46]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:45]([CH3:55])([CH3:54])[CH2:44][CH2:43]1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH2:8]([C@@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:30])[C@@H:22]([C@H:42]1[N:46]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:45]([CH3:55])([CH3:54])[CH2:44][CH2:43]1)[C:23]1[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 54374212HCID 54374212, compoundHCID 59564912HCID 59564912, compound

Product 1

HCID 68733649HCID 68733649, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

TiCl4 in toluene (3.52 mL, 3.52 mmol) was added to a solution of (R)-4-benzyl-3-(2-(4-bromophenyl)acetyl)oxazolidin-2-one (1.26 g, 3.35 mmol) in DCM (30 mL) at −78° C. DIEA (0.64 mL, 3.69 mmol) was then added to the cold stirring solution. The reaction was stirred at −78° C. for 15 minutes, followed by the addition of a solution of tert-butyl 5-methoxy-2,2-dimethylpyrrolidine-1-carboxylate (1.00 g, 4.36 mmol, see Example F) in DCM (10 mL). The reaction was then warmed to −10° C. and stirred for 2 hours. The reaction was quenched with a saturated NH4Cl solution (20 mL), and the organic fraction was isolated, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography to give (S)-tert-butyl 5-((R)-2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(4-bromophenyl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate (1.63 g, 85%) as a solid.

Workup

  1. temperatureThe reaction was then warmed to −10° C.
  2. stirringstirred for 2 hours
  3. customThe reaction was quenched with a saturated NH4Cl solution (20 mL)
  4. customthe organic fraction was isolated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-cf3cf9d6a3d94336816484f8a32dce5a
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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