Water → 5-(tert-Butyldiphenylsilyloxy)-N-isopropylpentan-1-amine

HRID 1485822Notes

Reaction equation

HRID 1485822 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH:7]([NH2:10])([CH3:9])[CH3:8].[C:11]([Si:15]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]I)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])([CH3:13])[CH3:12].O>C1COCC1>[Si:15]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:10][CH:7]([CH3:9])[CH3:8])([C:11]([CH3:12])([CH3:13])[CH3:14])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 100039911,1'-((1,1-Dimethylethyl)((5-iodopentyl)oxy)silylene)bis(benzene)

Product 1

HCID 708552025-(tert-Butyldiphenylsilyloxy)-N-isopropylpentan-1-amineYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

K2CO3 (1.50 g, 11.05 mmol), isopropylamine (0.65 mL, 11.05 mmol) and iodide 3 (2.50 g, 5.83 mmol) in dry THF (15 mL) were heated at 66° C. in a sealed tube under an argon atmosphere. After 12 h, water (5 mL) was added to the reaction mixture which was then extracted with EtOAc (3×50 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to afford 4 as a colorless liquid (1.90 g, 92%) sufficiently pure it was used without further purification. TLC:MeOH/CH2Cl2 (1:4), Rf˜0.30; 1H NMR (400 MHz) δ 7.65-7.67 (m, 4H), 7.30-7.40 (m, 6H), 3.65 (t, J=6.4 Hz, 2H), 2.70-2.82 (m, 1H), 2.55 (t, J=7.3 Hz, 2H), 1.50-1.64 (m, 2H), 1.32-1.50 (m, 4H), 1.05 (d, J=5.8 Hz, 3H), 1.04 (s, 9H); 13C NMR (100 MHz) δ 135.68, 134.21, 129.63, 127.70, 63.95, 48.81, 47.64, 32.60, 30.27, 27.0, 23.76, 23.15, 19.34.

Workup

  1. extractionwas then extracted with EtOAc (3×50 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ce6837bc954463aa2c56e84c9c24cbe
Source dataset
uspto-grants-2016_08
Patent number
US09422318B2

Reaction notes

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