Carbon tetrabromide → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-bromopropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

HRID 505261Notes

Reaction equation

HRID 505261 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH:30](O)[CH2:31][CH3:32])[C@H:14]2[CH3:34])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(Br)(Br)(Br)[Br:38].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH:30]([Br:38])[CH2:31][CH3:32])[C@H:14]2[CH3:34])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86628753(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-hydroxypropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 57617882(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-bromopropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-hydroxypropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (212.4 mg, 0.402 mmol) in CH2Cl2 (5 mL) was added CBr4 (333 mg, 1.00 mmol) and a solution of PPh3 (250 mg, 0.956 mmol) in CH2Cl2 (5 mL). The reaction was allowed to warm to room temperature. After 72 hours, the reaction was concentrated and purified by flash chromatography (10 to 50% EtOAc/hexanes) to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-bromopropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. LCMS=594.1 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.89-7.46 (m, 6H), 5.81-5.69 (m, 1H), 5.25-4.97 (m, 2H), 4.36-3.83 (m, 2H), 2.46-2.34 (m, 1H), 2.25-2.14 (m, 1H), 1.29-1.01 (m, 3H), 0.83-0.78 (m, 3H).

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by flash chromatography (10 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-368793ebc0434341abbb09c248a856b8
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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