tert-Butyldimethylsilyl chloride → 4-(2-((Tert-butyldimethylsilyl)oxy)ethyl)piperidine hydrochloride
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[C:19]([Si:23]([CH3:26])([CH3:25])[Cl:24])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[ClH:24].[C:19]([Si:23]([CH3:26])([CH3:25])[O:9][CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)([CH3:22])([CH3:21])[CH3:20]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
4-Piperidineethanol (2 g, 15.5 mmol) and N,N-diisopropylethylamine (3.00 g, 4.06 ml, 23.2 mmol) were combined with dichloromethane (50 mL) to give a colorless solution. t-Butyldimethylchlorosilane (2.8 g, 18.6 mmol) in dichloromethane (30 mL) was added to this solution during 15 min at 0° C. The reaction mixture was stirred for 2.5 h at 0° C. and afterwards for 21 h at room temperature. Subsequently the reaction mixture was concentrated in vacuo and the residue was crystallized from ethyl acetate and n-heptane (100 ml, 1:1) to give the title compound (3.45 g, 80%) as light yellow solid; GC-MS (EI) 243.0 (M)+.
Workup
- customto give a colorless solution
- concentrationSubsequently the reaction mixture was concentrated in vacuo
- customthe residue was crystallized from ethyl acetate and n-heptane (100 ml, 1:1)
Sources & evidence
- ORD record
- ord-48c65854be644fd5ad761ae5c4acbcce
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08648099B2
Reaction notes
Loading…