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Acetic Acid → [1,1-Dimethyl-2-(5-fluoro-2-methylphenylamino)ethyl]carbamic acid t-butyl ester

HRID 1694941
Notes
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Reaction equation

HRID 1694941 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20](=[O:27])[NH:21][C:22]([CH3:26])([CH3:25])[CH:23]=O)([CH3:18])([CH3:17])[CH3:16].[F:28][C:29]1[CH:30]=[CH:31][C:32]([CH3:36])=[C:33]([CH:35]=1)[NH2:34].C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:15]([O:19][C:20](=[O:27])[NH:21][C:22]([CH3:26])([CH3:25])[CH2:23][NH:34][C:33]1[CH:35]=[C:29]([F:28])[CH:30]=[CH:31][C:32]=1[CH3:36])([CH3:18])([CH3:17])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 677745-Fluoro-o-toluidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

Product 1

HCID 66645553[1,1-Dimethyl-2-(5-fluoro-2-methylphenylamino)ethyl]carbamic acid t-butyl ester
Yield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.9 g of sodium triacetoxyborohydride (32.5 mmol) was added to a solution of 5.08 g of (1,1-dimethyl-2-oxoethyl)carbamic acid t-butyl ester obtained in Reference Example 3 (27.1 mmol), 5 g of 5-fluoro-2-methylaniline (27.1 mmol) and 1.55 ml of acetic acid (27.1 mmol) in methylene chloride (270 ml) under ice-cooling, and the mixture was stirred at room temperature for 16 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with methylene chloride. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=8/1) to obtain 5.68 g of the title compound (yield: 71%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with methylene chloride
  3. washThen, the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-0c25bbc82dd6437eb3d1d4574c31bf1f
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158790B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes