Benzyl Bromide → HCID 66625271, compound

HRID 238573Notes

Reaction equation

HRID 238573 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:22])[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:7]([CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])[CH2:6][O:5]1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([O:21][C@H:16]([C@@H:7]1[CH2:6][O:5][C:4]([CH3:22])([CH3:3])[N:8]1[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C:17]([F:18])([F:20])[F:19])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10946477(S)-tert-butyl 2,2-dimethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)oxazolidine-3-carboxylate

Product 1

HCID 66625271HCID 66625271, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (60% in mineral oil, 300.0 mg, 7.50 mmol) in DMF (20 mL) was added (S)-tert-butyl 2,2-dimethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)oxazolidine-3-carboxylate (1.09 g, 3.64 mmol) in DMF (20 mL) and the mixture was stirred at room temperature for 1 h. Then, benzyl bromide (0.86 mL, 7.23 mmol) was added and the mixture was stirred at room temperature overnight then quenched with ice-water, extracted with EtOAc. The organic extracts were washed with water, brine and dried over Na2SO4. Removal of the solvent gave a residue, which was purified by silica gel chromatography to give (S)-tert-butyl 4-((R)-1-(benzyloxy)-2,2,2-trifluoroethyl)-2,2-dimethyloxazolidine-3-carboxylate (1.21 g, 85%), which showed a complicated NMR spectrum because of the different rotamers. 1H NMR (400 MHz, CDCl3, δ in ppm) 7.28˜7.33 (m, 5H), 4.60˜4.85 (m, 3H), 3.93˜4.23 (m, 3H), 1.42˜1.65 (m, 15H).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customthen quenched with ice-water
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent
  7. customgave a residue, which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-53b0cd1b662f44b284928312b7dab358
Source dataset
uspto-grants-2014_02
Patent number
US08642632B2

Reaction notes

Loading…