Water → HCID 86618694, compound

HRID 2239368Notes

Reaction equation

HRID 2239368 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].O>C(Cl)Cl>[CH3:33][S:34]([O:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86618693HCID 86618693, compound

Product 1

HCID 86618694HCID 86618694, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl (2S)-2-({[6-(hydroxymethyl)pyridin-2-yl]oxy}methyl)piperidine-1-carboxylate (520 mg, 1.61 mmol) and DIPEA (0.842 ml, 4.84 mmol) dissolved in DCM (10 ml) was cooled using an ice bath. Methanesulfonyl chloride (0.191 ml, 2.419 mmol) was added and the reaction stirred for 2 h. DCM (150 ml) and water (150 ml) were added and the phases separated. The organic phase washed with water (150 ml), dried through a phase separator and evaporated in vacuo, yielding the title compound as a light yellow oil (672 mg (104%)) which was used directly in the next step without further purification. MS (ESI+) 401.20 (M+1H+)

Workup

  1. temperaturewas cooled
  2. customthe phases separated
  3. washThe organic phase washed with water (150 ml)
  4. customdried through a phase separator
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3ca98dd75cbd434a8fc3999aa13fa4eb
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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