Triethylamine → Isopropyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylate

HRID 423576Notes

Reaction equation

HRID 423576 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57930058HCID 57930058, compound

Product 1

HCID 57930057Isopropyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylateYield 107.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-methylethyl 4-(hydroxymethyl)-1-piperidinecarboxylate (prepared as in Example 9, Step 1, 0.5 g, 2.36 mmol) in CH2Cl2 (5 mL) was cooled to 0° C. Et3N (0.5 mL, 3.54 mmol) was added, followed by dropwise addition of methanesulfonyl chloride (0.2 mL, 2.60 mmol). The reaction mixture was allowed to warm up to ambient temperature and stirred for 1 h and diluted with CH2Cl2. The mixture was washed with water, saturated aqueous NaHCO3, brine and dried over Na2SO4, filtered, and the filtrate was concentrated to give 0.71 g of the crude 1-methylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate as a light brown solid, which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 4.90 (septet, 1H, J=6.2 Hz), 4.25-4.15 (m, 2H), 4.06 (d, 2H, J=6.6 Hz), 3.01 (s, 3H), 2.80-2.65 (m, 2H), 2.00-1.85 (m, 1H), 1.80-1.65 (m, 2H), 1.30-1.15 (m, 8H).

Workup

  1. washThe mixture was washed with water, saturated aqueous NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-99441cea3747405db83e6ae7dd95035b
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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