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

HRID 1771175Notes

Reaction equation

HRID 1771175 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][NH:21][CH2:22]C)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CNCCO>>[Si:1]([O:18][CH2:19][CH2:20][NH:21][CH3:22])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 580801592-(tert-butyldiphenylsilyloxy)-N-ethylethanamine

Product 1

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineYield 49%

Procedure

The title compound (4.1 g, yield: 49%) was prepared using a procedure similar to the one described for the synthesis of INTERMEDIATE 23 utilizing 2-(methylamino)ethanol (2.0 g, 26.6 mmol) as starting material. The title product was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% DCM/10% MeOH in DCM with 1% NH4OH).

Workup

  1. customThe title product was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% DCM/10% MeOH in DCM with 1% NH4OH)

Sources & evidence

ORD record
ord-3fad27d1a1384253814e4caaa74422eb
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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