Hydrochloric Acid → HCID 49835452, compound

HRID 1752312Notes

Reaction equation

HRID 1752312 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.Cl[C:22]([O:24][CH:25]1[CH:32]2[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:34][CH:26]1[CH2:27]3)[CH2:31]2)=[O:23].Cl>C(Cl)Cl>[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:22]([O:24][CH:25]2[CH:26]3[CH2:34][CH:30]4[CH2:29][CH:28]([CH2:33][CH:32]2[CH2:31]4)[CH2:27]3)=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2618922-PhenylpyrrolidineHCID 108785372-adamantyl Chloroformate

Product 1

HCID 49835452HCID 49835452, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vial equipped with a flea stir bar was charged with 2-phenylpyrrolidine (17 mg, 0.12 mmol), i-Pr2NEt (0.031 mL, 0.17 mmol). A solution of 2-adamantyl chloroformate (25 mg, 0.12 mmol) in CH2Cl2 (1.5 mL) was added. The mixture was stirred over the weekend and applied to a 10-mL ChemElut cartridge prewetted with 5% aq HCl (5 mL). The cartridge was eluted with ether (20 mL). The eluate was concentrated and the residue was purified by prep HPLC to afford the title compound (24 mg, 63%). LC-MS Method 2 tR=11.81 min, m/z=326, 1H NMR (CDCl3) 0.92 (m, 1H), 1.03 (m, 1H), 1.30-2.20 (14H), 2.32 (m, 1H), 2.50 (br s, 1H), 3.64 (m, 2H), 4.70-5.10 (2H), 7.18 (m, 3H), 7.28 (m, 2H).

Workup

  1. customA vial equipped with a flea
  2. stirringThe mixture was stirred over the weekend
  3. washThe cartridge was eluted with ether (20 mL)
  4. concentrationThe eluate was concentrated
  5. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-3493ce74171b4f18864cb625164d4db8
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

Loading…