2-(Methylamino)ethanol → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

HRID 572789

Reaction equation

HRID 572789 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Si:17]([O:5][CH2:4][CH2:3][NH:2][CH3:1])([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineYield 53%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-(methylamino)ethanol (2.14 mL, 26.6 mmol) in DCM (60 mL) was added triethylamine (4.1 mL, 29.3 mmol),N,N-dimethylpyridin-4-amine (1.63 g, 13.3 mmol) and tert-butylchlorodiphenylsilane (7.6 mL, 29.3 mmol). The reaction was stirred overnight at 40° C. After cooling to RT, the reaction was quenched with water (20 mL) and ether (100 mL). The organic phase was washed with water, brine, dried over magnesium sulfate and concentrated to afford the crude product which was purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM. The solvent was evaporated to dryness to afford 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine (4.4 g, 53%) as a colorless oil. NMR Spectrum (DMSOd6): 0.99 (s, 9H), 2.27 (s, 3H), 2.63 (t, 2H), 3.68 (t, 2H), 7.40-7.49 (m, 6H), 7.60-7.65 (m, 4H).

Workup

  1. temperatureAfter cooling to RT
  2. customthe reaction was quenched with water (20 mL) and ether (100 mL)
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto afford the crude product which
  7. customwas purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM
  8. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-fda01a43cee343629498adfbe2f2e243
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Linked notes

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