Triethylamine → HCID 55131721, compound

HRID 1528194Notes

Reaction equation

HRID 1528194 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1.[N+:14]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21])([O-:16])=[O:15]>ClCCl>[OH:13][CH:10]1[CH2:11][CH2:12][N:8]([C:20]([C:19]2[CH:23]=[CH:24][CH:25]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=2)=[O:21])[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 982104-Hydroxypyrrolidine

Product 1

HCID 55131721HCID 55131721, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2.22 g of triethylamine (20 mmol), followed by 1.74 g of pyrrolidin-3-ol (20 mmol), were added to a solution of 3.71 g of 3-nitrobenzoyl chloride (20 mmol) in 40 ml of dichloromethane cooled to 0° C. The reaction medium was stirred at ambient temperature for 2 hours and was then diluted with 50 ml of dichloromethane. The organic phase was washed with 50 ml of a 1 N hydrochloric acid solution and then with 50 ml of a saturated sodium hydrogen carbonate solution, dried over magnesium sulfate and evaporated. 3.78 g of (3-hydroxypyrrolidin-1-yl)-(3-nitrophenyl)methanone were obtained and used without purification in the next step. Yield=80%.

Workup

  1. washThe organic phase was washed with 50 ml of a 1 N hydrochloric acid solution
  2. dry with materialwith 50 ml of a saturated sodium hydrogen carbonate solution, dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-1a16ec77c68249bcbb30e336adef5088
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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