tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate → HCID 90386997, compound

HRID 1476849Notes

Reaction equation

HRID 1476849 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:13]#[N:14])[N:4]=1.[OH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.[Ag+]>[C:13]([C:5]1[N:4]=[C:3]([CH2:2][O:15][C@H:16]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]2)[C:12]2[C:7]([CH:6]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)#[N:14]

Participants

5

Reactant 2

HCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 90386835HCID 90386835, compound

Product 1

HCID 90386997HCID 90386997, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent

Procedure

To 1-(bromomethyl)isoquinoline-3-carbonitrile (0.150 g, 0.607 mmol) in DCM (6 mL) was added (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (0.114 g, 0.607 mmol) and AgOTf (0.016 g, 0.061 mmol). The suspension was stirred for 15 minutes at RT and then heated at 45° C. overnight. The reaction mixture was subsequently cooled, absorbed onto silica and eluted with a gradient of 0-5% MeOH in DCM. The enriched fractions were concentrated in vacuo to give the title compound as a yellow residue which was used without further purification (54.6 mg, 25.4%). ESI-MS m/z [M+H-tert butyl]+ 298.6.

Workup

  1. temperatureheated at 45° C. overnight
  2. temperatureThe reaction mixture was subsequently cooled
  3. customabsorbed onto silica
  4. washeluted with a gradient of 0-5% MeOH in DCM
  5. concentrationThe enriched fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-d36aac99be694311b39285daa80e76e5
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…