Methyl chloroformate → HCID 66734710, compound

HRID 1963328Notes

Reaction equation

HRID 1963328 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8][NH:7]1.CCN(C(C)C)C(C)C.[C:32](Cl)(=[O:35])[O:33][CH3:34]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:18]=1)[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8][N:7]1[C:32]([O:33][CH3:34])=[O:35]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731845HCID 66731845, compound

Product 1

HCID 66734710HCID 66734710, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)piperidine-4-carboxylate (4.10 g, 12.84 mmol) in DCM (50 mL) cooled in an ice-bath was added DIPEA (3.5 mL, 20.09 mmol) followed by methyl carbonochloridate (1.112 mL, 14.12 mmol). After completed addition the reaction mixture was stirred at room temperature for 2 h. The solvents were evaporated and the residue partitioned between ethyl acetate and 3.8 M HCl. After phase separation the organic layer was washed with brine, then dried over MgSO4 and evaporated to yield crude dimethyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)piperidine-1,4-dicarboxylate (4.94 g, 102%) as a pale yellow oil. MS m/z 378 (M+H)+

Workup

  1. additionaddition the reaction mixture
  2. customThe solvents were evaporated
  3. customthe residue partitioned between ethyl acetate and 3.8 M HCl
  4. customAfter phase separation the organic layer
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-a3805e1e57124cf484b411a1fccacb1c
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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