Methyl chloroformate → HCID 66735198, compound

HRID 1963295Notes

Reaction equation

HRID 1963295 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][NH:10]2)=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[C:32](Cl)(=[O:35])[O:33][CH3:34]>C(Cl)Cl>[F:22][C:2]([F:21])([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][N:10]2[C:32]([O:33][CH3:34])=[O:35])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732369HCID 66732369, compound

Product 1

HCID 66735198HCID 66735198, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(4-(trifluoromethoxy)benzyl)piperidine-4-carboxylate (8.19 g, 25.81 mmol) in DCM (100 mL) was added DIPEA (5.40 mL, 30.97 mmol) followed by methyl carbonochloridate (2.236 mL, 28.39 mmol). The reaction mixture was stirred at room temperature for 30 min. The solvents were evaporated and the residue partitioned between ethyl acetate and 3.8 M HCl. After phase separation the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and evaporated to give a yellow oil. Dimethyl 2-(4-(trifluoromethoxy)benzyl)piperidine-1,4-dicarboxylate (9.72 g, 100%) was isolated. MS m/z 376 (M+H)+

Workup

  1. customThe solvents were evaporated
  2. customthe residue partitioned between ethyl acetate and 3.8 M HCl
  3. customAfter phase separation the aqueous layer
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customevaporated
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-35adb3ecf2884a589d94361a7db2acdf
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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