Triethylamine → HCID 71113880, compound

HRID 57535Notes

Reaction equation

HRID 57535 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH:13]([CH2:15]O)[CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:36]=[N+:37]=[N-:38].[Na+]>ClCCl.C(OCC)C.CCOC(C)=O.CCCCCC>[N:36]([CH2:15][CH:13]1[CH2:14][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1)=[N+:37]=[N-:38]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 50896320Tert-butyl 3-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 71113880HCID 71113880, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of tert-butyl 3-(tert-butyldimethylsilyloxy)-5-(hydroxymethyl)piperidine-1-carboxylate from step B in dichloromethane (50 mL) was added triethylamine (4.67 g, 46.2 mmol) and methanesulfonyl chloride (2.65 g, 23.1 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1.5 hours, then diluted with diethyl ether, washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude residue was dissolved in NMP. Sodium azide (3.00 g, 46.2 mmol) was added, and the resulting suspension was stirred at 80° C. overnight. The reaction mixture was diluted with EtOAc/hexane, washed with brine, then dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound. MS (m/z): 271 (M-Boc+H)+.

Workup

  1. washwashed with saturated sodium bicarbonate solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude residue was dissolved in NMP
  6. stirringthe resulting suspension was stirred at 80° C. overnight
  7. washwashed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4fff65519f424a998e91f885e52871ce
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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