Diethyl Ether → HCID 57420555, compound

HRID 30408Notes

Reaction equation

HRID 30408 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:15]O)([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:24][S:25](Cl)(=[O:27])=[O:26].CCOCC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:15][S:25]([CH3:24])(=[O:27])=[O:26])([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22258928Tert-butyl 3-(hydroxymethyl)-3-methylpiperidine-1-carboxylate

Product 1

HCID 57420555HCID 57420555, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. stirred solution of Intermediate 55 (0.844 g, 3.68 mmol) in dry CH2Cl2 (25 ml) was added Et3N (0.513 ml, 3.682 mmol) and the reaction was stirred for 15 minutes. Methansulfonyl chloride (0.285 ml, 3.682 mmol) was added dropwise and the reaction was allowed to warm to room temperature overnight with good stirring. The reaction was complete by TLC, and Et2O (100 ml) was added. The mixture was filtered and the filter caked was washed with additional Et2O. The filtrate was then concentrated under reduced pressure. The residue was chromatographed with hexanes/EtOAc (0>25%) to yield 1.05 g (93.1%) of 3-methanesulfonylmethyl-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 56). 1H NMR (400 MHz, CDCl3) δ ppm 1.0 (s, 3 H), 1.4 (m, 1 H), 1.4 (s, 9 H), 1.6 (m, 3 H), 3.0 (s, 3 H), 3.2 (s, 1 H), 3.5 (s, 2 H), 4.0 (d, J=2.4 Hz, 2 H).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. washthe filter caked was washed with additional Et2O
  4. concentrationThe filtrate was then concentrated under reduced pressure
  5. customThe residue was chromatographed with hexanes/EtOAc (0>25%)

Sources & evidence

ORD record
ord-786aff377e384a54b03121697a243557
Source dataset
uspto-grants-2008_09
Patent number
US07423054B2

Reaction notes

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