Trichloroacetyl chloride → tert-Butyl 4-(cyanomethoxy)piperidine-1-carboxylate

HRID 221345Notes

Reaction equation

HRID 221345 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16](=O)[NH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][CH2:15][C:16]#[N:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 578567294-Carbamoylmethoxypiperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 45496680tert-Butyl 4-(cyanomethoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-carbamoylmethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 13, 235 mg, 0.91 mmol) and triethylamine (140 μl, 1 mmol) in anhydrous CH2Cl2 (5 ml) was cooled to 0° C. and a solution of trichloroacetyl chloride (174 mg, 0.96 mmol) in anhydrous CH2Cl2 added dropwise. The reaction mixture was stirred at rt for 1 h, the solvent was removed and the residue purified by flash chromatography (IH-EtOAc, 1:1) to afford the title compound: δH (CDCl3) 1.50 (9H, s), 1.58-1.65 (2H, m), 1.89-1.95 (2H, m), 3.20 (2H, m), 3.74-3.79 (3H, m), 4.33 (2H, s).

Workup

  1. customthe solvent was removed
  2. customthe residue purified by flash chromatography (IH-EtOAc, 1:1)

Sources & evidence

ORD record
ord-e9fc727771d847b1917045fded0eff83
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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