Methyl chloroformate → HCID 66734590, compound

HRID 1963337Notes

Reaction equation

HRID 1963337 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([F:21])[C:19]=1[F:20])[CH2:6][CH:7]1[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][NH:8]1.CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:34])[O:32][CH3:33]>C(Cl)Cl>[F:21][C:18]1[CH:17]=[C:5]([CH:4]=[C:3]([F:2])[C:19]=1[F:20])[CH2:6][CH:7]1[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][N:8]1[C:31]([O:32][CH3:33])=[O:34]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731834HCID 66731834, compound

Product 1

HCID 66734590HCID 66734590, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(3,4,5-trifluorobenzyl)piperidine-4-carboxylate hydrochloride (3.957 g, 12.22 mmol) and DIPEA (4.68 mL, 26.89 mmol) were dissolved in DCM (20 mL) and methyl carbonochloridate (1.059 mL, 13.45 mmol) was added. The reaction was stirred at room temperature for 18 h, diluted with DCM (200 mL), washed with 0.1 M HCl (2×200 mL), satd NaHCO3 (200 mL), dried through a phase separator and evaporated in vacuo to yield dimethyl 2-(3,4,5-trifluorobenzyl)piperidine-1,4-dicarboxylate (4.01 g, 95%) as a brown oil. MS m/z 346 (M+H)+

Workup

  1. washwashed with 0.1 M HCl (2×200 mL), satd NaHCO3 (200 mL)
  2. customdried through a phase separator
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-013b9f41577f4b4e9a869463e05e7a1e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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