Triethylamine → HCID 11695663, compound

HRID 1052220Notes

Reaction equation

HRID 1052220 reaction equation
[C:1]([CH:3]([OH:18])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)#[N:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[C:1]([CH:3]([O:18][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:9][CH2:10]1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 73013690HCID 73013690, compound

Product 1

HCID 11695663HCID 11695663, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(2-cyano-2-hydroxyethyl)piperidine-1-carboxylate (67.0 g) and triethylamine (35.0 g) in dichloromethane (500 mL) was slowly added a solution of methanesulfonyl chloride (36.3 g) in dichloromethane (200 mL). The reaction system was stirred at room temperature for 2 hr, and added to ice water (300 mL). The organic layer was dried over anhydrous sodium sulfate, insoluble material was removed by filtration, and the filtrate was concentrated to give the title compound (80.0 g).

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate, insoluble material
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-65dc9e3254e24df99e50aceefa7951a6
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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