Water → N-(2-(tert-butyldimethylsilyloxy)ethyl)-1,1,1-trifluoropropan-2-amine

HRID 2169183Notes

Reaction equation

HRID 2169183 reaction equation
[F:1][C:2]([F:10])([F:9])[CH:3]([NH:5][CH2:6][CH2:7][OH:8])[CH3:4].C(N(C(C)C)CC)(C)C.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].O>ClCCl>[Si:20]([O:8][CH2:7][CH2:6][NH:5][CH:3]([CH3:4])[C:2]([F:10])([F:9])[F:1])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 86725833Ethanol, 2-[(2,2,2-trifluoro-1-methylethyl)amino]-

Product 1

HCID 86725834N-(2-(tert-butyldimethylsilyloxy)ethyl)-1,1,1-trifluoropropan-2-amineYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(1,1,1-trifluoropropan-2-ylamino)ethanol (40) (5.50 g, 35.0 mmol, Eq: 1.00) in dichloromethane (100 ml) were added diisopropylethylamine (6.33 g, 8.56 ml, 49.0 mmol, Eq: 1.4) followed by tert-butyldimethylsilyl chloride (5.8 g, 38.5 mmol, Eq: 1.1) at room temperature under a nitrogen atmosphere. The resulting solution was stirred for 16 hrs and then it was poured into water (100 ml) and the organic layer was separated, washed with brine, dried (MgSO4), concentrated, and chromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane) to obtain N-(2-(tert-butyldimethylsilyloxy)ethyl)-1,1,1-trifluoropropan-2-amine (41) (oil, 3.52 g, 13.0 mmol, 37.1% yield).

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4befe3b937804849a6ba97f7d1aedff0
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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