Methyl chloroformate → Tert-butyl 4-{1-[(methoxycarbonyl)oxy]-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl}piperidine-1-carboxylate

HRID 1895991Notes

Reaction equation

HRID 1895991 reaction equation
[OH:1][CH:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1.C(N(CC)CC)C.Cl[C:33]([O:35][CH3:36])=[O:34]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:36][O:35][C:33]([O:1][CH:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1)=[O:34]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 68725592Tert-butyl 4-[1-hydroxy-3-(6-methylpyridin-2-yl)prop-2-ynyl]piperidine-1-carboxylate

Product 1

HCID 68725060Tert-butyl 4-{1-[(methoxycarbonyl)oxy]-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the Compound of Example 39 (50 mg, 0.15 mmol), triethylamine (65 μL, 0.45 mmol) and 4-dimethylaminopyridine (10 mg, 0.07 mmol) in 3 mL of CH2Cl2 cooled at 0-5° C., methyl chloroformate (23 μL, 0.30 mmol) was added dropwise. The reaction mixture was stirred at r.t. overnight. Afterwards, it was evaporated to dryness and purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 8:2 affording the title product (0.28 g) as a brown oil.

Workup

  1. customAfterwards, it was evaporated to dryness
  2. custompurified by automated flash liquid chromatography (Horizon™-Biotage)
  3. washeluting with Petroleum Ether-EtOAc 8:2 affording the title product (0.28 g) as a brown oil

Sources & evidence

ORD record
ord-17c29791f4a243a9bda0fb8fea311f67
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…