Methyl chloroformate → HCID 23536848, compound

HRID 1867368Notes

Reaction equation

HRID 1867368 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CCN(CC)CC.Cl[C:23]([O:25][CH3:26])=[O:24].OS([O-])(=O)=O.[K+]>C(Cl)Cl>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:23]([O:25][CH3:26])=[O:24])[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 23536848HCID 23536848, compoundYield 638.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.00 g (2.00 mmol) of 4-amino-1-BOC-piperidine and 4.18 ml (3.00 mmol) of Et3N in 50 ml of CH2Cl2 was treated at 0° C. with 1.62 ml (2.10 mmol) of methyl chloroformate. The reaction was stirred for 16 h at RT, neutralized with aqueous 10% KHSO4 and extracted with CH2Cl2 (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (n- heptane/EtOAc 1:1 to 1:2) to yield 3.30 g (64%) of the title compound as white solid. MS: 259.2 (MH+).

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. washThe organic phases were washed with aqueous 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. custompurified by flash silica gel column (n- heptane/EtOAc 1:1 to 1:2)

Sources & evidence

ORD record
ord-e3f721e56e61429c994b3586a1c4a6f2
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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