N,N-Bis(trimethylsilyl)trifluoroacetamide → HCID 86697918, compound

HRID 338104Notes

Reaction equation

HRID 338104 reaction equation
[CH2:1]([N:4]1[CH2:8][C:7]([NH2:15])([C:9]2[S:10][CH:11]=[C:12]([Br:14])[CH:13]=2)[CH:6]([CH2:16][OH:17])[CH2:5]1)[CH:2]=[CH2:3].C[Si](N([Si](C)(C)C)C(=[O:28])C(F)(F)F)(C)C.[C:33]([N:41]=[C:42]=S)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[CH2:1]([N:4]1[CH2:5][CH:6]([CH2:16][OH:17])[C:7]([NH:15][C:42]([NH:41][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:28])([C:9]2[S:10][CH:11]=[C:12]([Br:14])[CH:13]=2)[CH2:8]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 68284Benzoyl isothiocyanateHCID 86697919HCID 86697919, compound

Product 1

HCID 86697918HCID 86697918, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-allyl-4-amino-4-(4-bromo-2-thienyl)pyrrolidin-3-yl]methanol 4 g, 12.6 mmol) in tetrahydrofuran (180 mL) is added bis(trimethylsilyl)trifluoroacetamide (3.2 g, 12.6 mmol) and the reaction is stirred at room temperature for 1 hr. Benzoyl isothiocyanate (2.5 g, 15.1 mmol) is added in one portion, stirred for 1 hour at room temperature, and then quenched with 1 N hydrochloric acid (20 mL). After stirring for 1 hour the pH of the reaction is adjusted to >8 using saturated sodium bicarbonate and extracted with dichloromethane. The organic phases are combined, concentrated under reduced pressure, and triturated with hexane/ethyl acetate (4:1) to give the title compound (5.9 g, >95%). ES/MS (m/e) (79Br/81Br) 480/482 (M+H).

Workup

  1. stirringstirred for 1 hour at room temperature
  2. customquenched with 1 N hydrochloric acid (20 mL)
  3. stirringAfter stirring for 1 hour the pH of the reaction
  4. extractionextracted with dichloromethane
  5. concentrationconcentrated under reduced pressure
  6. customtriturated with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-64ed79c4157b49b6a64c110599d37cec
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

Loading…