Acetic Acid → [4-(Tert-butyldimethylsilanyloxy)cyclohexyl]-(2-iodophenyl)amine

HRID 1092415Notes

Reaction equation

HRID 1092415 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[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)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Si:9]([O:16][CH:17]1[CH2:18][CH2:19][CH:20]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[I:1])[CH2:21][CH2:22]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 119952-IodoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanone

Product 1

HCID 57675754[4-(Tert-butyldimethylsilanyloxy)cyclohexyl]-(2-iodophenyl)amineYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-iodoaniline (2.5 g, 10.9 mmol) in dichloromethane (160 mL) was added 4-(tert-butyldimethylsilanyloxy)cyclohexanone (2.39 g, 10.9 mmol) and acetic acid (8 mL). After the reaction was stirred for 1 hour at room temperature, sodium triacetoxyborohydride (3.47 g, 16.4 mmol) was added and the reaction was stirred at room temperature overnight. The reaction was quenched with saturated sodium bicarbonate and extracted with dichloromethane. The organic solution was dried (MgSO4) and concentrated to give 4.47 g of the desired amine, which was used without further purification. LC-MS (C15H30INOSi calc'd 431) m/z 432 (M+H).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe reaction was quenched with saturated sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic solution was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-25da072faa62424f96fb59f04daff3e1
Source dataset
uspto-grants-2012_03
Patent number
US08129424B2

Reaction notes

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