Acetic Acid → HCID 178455359, compound

HRID 2043329Notes

Reaction equation

HRID 2043329 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Si:9]([O:16][CH:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl.ClCCl>[C:12]([Si:9]([CH3:11])([CH3:10])[O:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=2)[CH2:19][CH2:18]1)([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 79323-ChloroanilineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanone

Product 1

HCID 178455359HCID 178455359, compoundYield 23.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloroaniline (1.27 g, 10 mmol) in 1,2-dichloroethane (20 ml) were added molecular sieves (4 g, size 0.4 nM) and 4-(tert-butyldimethylsilyloxy)-cyclohexanone (4.57 g, 20 mmol). After stirring the mixture for 30 min at room temperature sodium triacetoxyborohydride (8.48 g, 40 mmol) and acetic acid (1.2 g, 20 mmol) were added. The reaction mixture was stirred at room temperature overnight. For workup dichloromethane (100 ml) and 1 M sodium bicarbonate solution (40 ml) were added and the mixture was shaken. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (heptane/ethyl acetate=1:1) to yield a colourless liquid (0.80 mg, 23.5%); MS (EI): 339.2; 341.3 (M+.).

Workup

  1. additionwere added
  2. stirringthe mixture was shaken
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-295d87c888df44a083222393b7924dda
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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