Water → HCID 86608163, compound

HRID 593429Notes

Reaction equation

HRID 593429 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]([OH:8])[CH3:7])[CH2:2][CH3:3].[C:9]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])([CH3:11])[CH3:10].O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:13]([O:8][CH:6]([CH3:7])[CH2:5][NH:4][CH2:1][CH2:2][CH3:3])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 3806320HCID 3806320, compound

Product 1

HCID 86608163HCID 86608163, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(propylamino)propan-2-ol (8.00 g, 68.3 mmol), tert-butylchlorodimethylsilane (10.9 g, 72.4 mmol), and catalytic amount of DMAP in CH2Cl2 (68 mL) at 0° C. was added dropwise TEA (9.61 ml, 68.3 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. Additional 1 mL of TEA was added and stirred for additional 20 h. Water (60 mL) was added. The layers were separated. The aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was filtered again to afford quantitatively 2-(tert-butyldimethylsilyloxy)-N-propylpropan-1-amine that was used directly without further purification.

Workup

  1. stirringstirred for additional 20 h
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc (1×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude material that
  9. filtrationwas filtered again

Sources & evidence

ORD record
ord-38fdeb865d2a4cbd914f029d64f681a3
Source dataset
uspto-grants-2016_01
Patent number
US09242964B2

Reaction notes

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