Triethylamine → 3-(Tert-butyldiphenylsilanoxy)-2,2-dimethylpropylamine

HRID 589838Notes

Reaction equation

HRID 589838 reaction equation
[NH2:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][OH:5].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[Si:24](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.O>[O:5]([CH2:4][C:3]([CH3:7])([CH3:6])[CH2:2][NH2:1])[Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 94078tert-ButyldiphenylchlorosilaneHCID 1173261-Propanol, 3-amino-2,2-dimethyl-

Product 1

HCID 866808103-(Tert-butyldiphenylsilanoxy)-2,2-dimethylpropylamineYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution at 0° C. of 0.500 g (4.85 mmol) of 3-amino-2,2-dimethylpropanol (CAS 26734-09-8) in 12 ml of dichloromethane are added 0.059 g (0.48 mmol) of dimethylaminopyridine and 1.35 ml (9.7 mmol) of triethylamine. 1.60 g (5.82 mmol) of tert-butyldiphenylsilyl chloride dissolved in 5 ml of dichloromethane are then added dropwise. The mixture is stirred for 30 minutes at 0° C. and then for 2 hours at room temperature. 20 ml of water are then added. The organic phase is separated out by settling, washed with water and then with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure to give an oil, which is chromatographed on a column of aminopropyl silica gel, eluting with a mixture of 0 to 10% methanol in dichloromethane, to give 1.20 g of 3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropylamine in the form of a colourless oil.

Workup

  1. additionare then added dropwise
  2. waitfor 2 hours at room temperature
  3. customThe organic phase is separated out
  4. washwashed with water
  5. dry with materialwith saturated aqueous sodium chloride solution and dried over sodium sulfate
  6. customthe solvent is evaporated off under reduced pressure
  7. customto give an oil, which
  8. customis chromatographed on a column of aminopropyl silica gel
  9. washeluting with a mixture of 0 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-86a38d44fa52433c8a307984a2b4324e
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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