Methyl chloroformate → HCID 23536848, compound

HRID 1192653Notes

Reaction equation

HRID 1192653 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.Cl[C:16]([O:18][CH3:19])=[O:17].C(N(CC)CC)C>C(Cl)Cl>[CH3:19][O:18][C:16]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)=[O:17]

Participants

5

Reactant 3

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

Product 1

HCID 23536848HCID 23536848, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-aminopiperidine-1-carboxylate (0.1 g, 0.5 mmol) was combined with methyl chloroformate (0.046 mL, 0.59 mmol) and triethylamine (0.22 mL, 1.6 mmol) in methylene chloride (2 mL) at room temperature and stirred for 2 hours. The reaction was diluted with dichloromethane, washed with water, dried over MgSO4, and then concentrated. The resulting residue was purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give tert-butyl 4-[(methoxycarbonyl)amino]piperidine-1-carboxylate, LCMS [M+Na] 281.1. The later was treated with 4.57 M hydrogen chloride in 1,4-dioxane (1 mL, 4 mmol) at room temperature for 1 hour. The mixture was concentrated to give crude product which was used directly in the next step. LCMS calculated for C7H15N2O2 (M+H)+: m/z=159.1; Found: 159.1.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified on silica gel (eluting with 0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f94007b2ab104d269bc64020e7f9bde4
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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