Triethylamine → HCID 86666573, compound

HRID 2088892Notes

Reaction equation

HRID 2088892 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:6]=[C:5]1[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:35][S:36]([O:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[N:6]=[C:5]1[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)(=[O:38])=[O:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67113226tert-Butyl 4-(1-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 86666573HCID 86666573, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Combine tert-butyl 4-(1-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (4.40 g, 11.60 mmol) and triethylamine (4.9 mL, 3.0 eq) in dichloromethane (72 mL). Cool to 0° C. and add methanesulfonyl chloride (1.1 mL, 1.2 eq). After 1 hour, dilute with additional dichloromethane and saturated aqueous sodium bicarbonate. Separate the layers. Dry the organics over anhydrous sodium sulfate, filter, and concentrate in vacuo to give the title compound as a light yellow solid (5.05 g, 95%). MS (ES) m/z=458 [M]+.

Workup

  1. customSeparate the layers
  2. dry with materialDry the organics over anhydrous sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9bc6b42d2e2b4f8691aab4a77e957923
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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