Triethylamine → HCID 86629996, compound

HRID 656469Notes

Reaction equation

HRID 656469 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]2[CH2:25][OH:26])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH:13]2[CH2:25][O:26][S:35]([CH3:34])(=[O:37])=[O:36])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 68577163HCID 68577163, compound

Product 1

HCID 86629996HCID 86629996, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 10 mmol of tert-butyl 2-benzyl-6-hydroxymethyl-2,7-diazaspiro[4.5]decane-7-carboxylate in 30 ml of dichloromethane is admixed at 0° C. with 15 mmol of triethylamine, followed by 11 mmol of methanesulphonyl chloride. The reaction mixture is stirred at 0° C. for an hour and then at room temperature for an hour. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane. The combined organic extracts are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60 F) on the basis of the Rf value.

Workup

  1. waitat room temperature for an hour
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-662adb7e3bd445c29bc9b6f7df30c85c
Source dataset
uspto-grants-2011_12
Patent number
US08071773B2

Reaction notes

Loading…