Propylene Oxide → HCID 89725864, compound

HRID 592063Notes

Reaction equation

HRID 592063 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][CH2:9]1)=[O:7])=[O:2].[C:24](O)([C:26](F)(F)F)=[O:25].C1OC1C>C(Cl)Cl>[OH:25][CH:24]([CH3:26])[CH2:14][N:11]1[CH2:10][CH2:9][N:8]([C:6]([C:5]2[CH:4]=[C:3]([CH:23]=[CH:22][CH:21]=2)[CH:1]=[O:2])=[O:7])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 6422Trifluoroacetic acidHCID 89726095HCID 89726095, compound

Product 1

HCID 89725864HCID 89725864, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-formylbenzoyl)piperazine-1-carboxylate 21 (700 mg, 2. 2 mmol) in DCM (5 mL) was added TFA (1.75 mL, 1.54 mmol) at 0° C. The reaction mixture was stirred at room temperature for 3 h. After 3 h, RM was washed with 10% sodium bicarbonate solution and concentrated. The crude material was dissolved in methanol (4 mL) and propylene oxide (892 mg, 15.3 mmol) was added. The reaction was heated at 55° C. for 15 h. TLC analysis indicated complete consumption of starting material. The reaction mixture was concentrated and purification of crude material by column chromatography (3% MeOH/DCM, Silica (230-400)) afforded product as white sticky solid (100 mg, 16.4%).

Workup

  1. waitAfter 3 h
  2. washRM was washed with 10% sodium bicarbonate solution
  3. concentrationconcentrated
  4. dissolutionThe crude material was dissolved in methanol (4 mL)
  5. temperatureThe reaction was heated at 55° C. for 15 h
  6. customconsumption of starting material
  7. concentrationThe reaction mixture was concentrated
  8. custompurification of crude material by column chromatography (3% MeOH/DCM, Silica (230-400))

Sources & evidence

ORD record
ord-f886da89a14742d6a70f1d9a1a5f3b91
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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