(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 86720533, compound

HRID 1755240Notes

Reaction equation

HRID 1755240 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.Cl[C:15]1[C:16]2[N:17]([CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:19][N:20]=1>CCN(C(C)C)C(C)C.F[B-](F)(F)F.C([N+]1C=CN(C)C=1)CCC>[C:15]1([N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]2)[C:16]2[N:17]([CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:19][N:20]=1

Participants

5

Reactant 2

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 156620891-Chloropyrrolo[1,2-a]pyrazine

Product 1

HCID 86720533HCID 86720533, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 27341781-Butyl-3-methylimidazolium tetrafluoroborateCatalystHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (0.91 g, 4.9 mmol, 1 eq) in 2.6 mL of DIPEA was added 1-chloropyrrolo[1,2-a]pyrazine (0.75 g, 4.9 mmol, 1 eq) and 1 drop of 1-butyl-3-methylimidazolium tetrafluorborate. After heating for 3 h at 110° C., the mixture was concentrated and purified by silica gel flash chromatography (100% EtOAc) to afford (S)-tert-butyl N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)carbamate (0.88 g, 2.9 mmol, 59%).

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by silica gel flash chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-228a7335e43b45bd97b84bd104db831e
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

Loading…