1-Bromo-3-methylbutane → HCID 86615388, compound

HRID 1436743Notes

Reaction equation

HRID 1436743 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([OH:14])[CH2:11][CH2:10][C@@H:9]1[C@H:15]1[O:19][C:18]([CH3:21])([CH3:20])[N:17]([C:22](=[O:24])[CH3:23])[C@H:16]1[CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([O:14][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:11][CH2:10][C@@H:9]1[C@H:15]1[O:19][C:18]([CH3:20])([CH3:21])[N:17]([C:22](=[O:24])[CH3:23])[C@H:16]1[CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutane2×HCID 24758Sodium hydride2×HCID 86615389HCID 86615389, compound

Product 1

HCID 86615388HCID 86615388, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Add (2R, 5R)-2-{(4S, 5S)-3-Acetyl-4-[3,5-difluoro-benzyl]-2,2-dimethyl-oxazolidin-5-yl}-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.06 g, 0.13 mmol) in 1.0 mL dimethylformamide to 60% sodium hydride (0.006 g, 0.15 mmol) in 0.5 mL dimethylformamide at room temperature and stir for 15 minutes. Add 1-bromo-3-methylbutane (0.023 mL, 0.19 mmol) and stir at room temperature overnight. Add 60% sodium hydride (0.006 g, 0.15 mmol) and 1-bromo-3-methylbutane (0.023 mL, 0.19 mmol) and stir for 4 h at room temperature. Quench with water and extract with diethyl ether, dry the organic layer over magnesium sulfate and concentrate. Subject the residue to silica gel chromatography, eluting with 100% dichloromethane to 90:10 dichloromethane: ethyl acetate to provide the desired compound (0.05 g, 75%).

Workup

  1. stirringstir for 4 h at room temperature
  2. customQuench with water
  3. extractionextract with diethyl ether
  4. dry with materialdry the organic layer over magnesium sulfate
  5. concentrationconcentrate
  6. washeluting with 100% dichloromethane to 90:10 dichloromethane

Sources & evidence

ORD record
ord-381ec172feec45bd949a4245d049b420
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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