Hydrochloric Acid → HCID 86609654, compound

HRID 2111569Notes

Reaction equation

HRID 2111569 reaction equation
[C:1]1([C@@H:7]([N:9]([CH:16]2[CH2:25][CH2:24][C:19]3(OCC[O:20]3)[CH2:18][CH2:17]2)[C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>O1CCCC1>[C:1]1([C@@H:7]([N:9]([CH:16]2[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][CH2:17]2)[C:10](=[O:15])[C:11]([F:12])([F:14])[F:13])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86609653HCID 86609653, compound

Product 1

HCID 86609654HCID 86609654, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

N-((1S)-1-Phenylethyl)-N-(1,4-dioxaspiro[4.5]dec-8-yl)-2,2,2-trifluoroacetamide (15.31 g, 42.84 mmol) was dissolved in tetrahydrofuran (30 mL). The solution was treated with 30 mL of 3.0 N aqueous HCl. The reaction was heated to 50-60° C. over 48 h. The reaction was cooled to room temperature. THF was removed under reduced pressure. The crude product was extracted with dichloromethane and was purified by silica gel column (eluent 15-20% ethyl acetate in hexanes). The product was isolated as a yellow oil (5.49 g, 41% yield) M+1: 314.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customTHF was removed under reduced pressure
  3. extractionThe crude product was extracted with dichloromethane
  4. customwas purified by silica gel column (eluent 15-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-053b1bf25fd1428d9bafec208af7f292
Source dataset
uspto-grants-2009_04
Patent number
US07521446B2

Reaction notes

Loading…