Triethylamine → HCID 59428662, compound

HRID 504147Notes

Reaction equation

HRID 504147 reaction equation
Cl.[CH2:2]([O:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:25][C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>ClCCl>[CH2:2]([O:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[S:32]([C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=1)(=[O:34])=[O:33])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 66751061HCID 66751061, compound

Product 1

HCID 59428662HCID 59428662, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-piperidine-2-carboxylic acid benzyl ester hydrochloride (5.00 g, 19.5 mmol) and triethylamine (5.50 mL, 39.1 mmol) in dichloromethane (150 mL) was added 3-fluorobenzenesulfonyl chloride (3.80 g, 19.5 mmol). The mixture was stirred at room temperature for 5 h as it turned to a white suspension. The suspension was washed twice with distilled water. The organic layer was then dried over magnesium sulfate and concentrated to afford 9 g of crude oil. Flash column chromatography on silica gel (ethyl acetate/n-heptane) provided 6.51 g (88.3%) of the title compound as a yellow oil.

Workup

  1. washThe suspension was washed twice with distilled water
  2. dry with materialThe organic layer was then dried over magnesium sulfate
  3. concentrationconcentrated
  4. customto afford 9 g of crude oil

Sources & evidence

ORD record
ord-f390466176cf4ac198e682f2ec87f7c4
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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