Lithium Hexamethyldisilazide → HCID 67271943, compound

HRID 597841

Reaction equation

HRID 597841 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].Cl[CH2:20][O:21][CH2:22][CH2:23][Cl:24].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:24][CH2:23][CH2:22][O:21][CH2:20][C:3]1([C:1]#[N:2])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 102908101-chloro-2-(chloromethoxy)ethaneHCID 22028286Benzyl 4-cyanopiperidine-1-carboxylate

Product 1

HCID 67271943HCID 67271943, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 4-cyanopiperidine-1-carboxylate (10.0 g, 41 mmol) and 2-chloroethyl chloromethyl ether (6.3 mL, 49.2 mmol) in THF (80 mL) was cooled to −78° C. To this solution was added drop wise LiHMDS (50 mL, 50 mmol, 1N in THF) and the resulting mixture was gradually warmed to room temp over 5 h. The reaction was quenched with water and the organic phase was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (1:1 EtOAc/hexane) to give the title compound as yellow oil (11.9 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ: 7.33-7.31 (5H, m), 5.10 (2H, d, J=5.9 Hz), 4.21 (2H, bs), 3.79-3.76 (2H, m), 3.63-3.60 (2H, m), 3.52-3.51 (2H, m), 3.09 (2H, bs), 1.96-1.92 (2H, m), 1.55-1.51 (2H, m).

Workup

  1. customThe reaction was quenched with water
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-9af7343dc09e4601873c16461fc5d8db
Source dataset
uspto-grants-2011_03
Patent number
US07897593B2

Linked notes

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