Hydrochloric Acid → HCID 66883380, compound

HRID 72135Notes

Reaction equation

HRID 72135 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([NH:9][CH:10]2[CH:17]3[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:19][CH:11]2[CH2:12]4)[CH2:16]3)=[O:8])[CH2:3]1.CCN(C(C)C)C(C)C.Cl[C:30]([O:32][CH3:33])=[O:31].Cl>C(Cl)Cl>[CH:17]12[CH2:16][CH:15]3[CH2:14][CH:13]([CH2:12][CH:11]([CH2:19]3)[CH:10]1[NH:9][C:7]([N:4]1[CH2:5][CH2:6][C@@H:2]([NH:1][C:30](=[O:31])[O:32][CH3:33])[CH2:3]1)=[O:8])[CH2:18]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66884414HCID 66884414, compound

Product 1

HCID 66883380HCID 66883380, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vial equipped with a flea stir bar was charged with (R)-3-amino-N-(2-adamantyl)pyrrolidine-1-carboxamide (25 mg, 0.095 mmol), i-Pr2NEt (0.07 mL, 0.38 mmol) and CH2Cl2. The solution was stirred and methyl chloroformate (0.009 mL, 0.11 mmol) was added. The mixture was stirred overnight at rt and applied to a 10-mL ChemElut cartridge prewetted with 5% aq HCl (6 mL). The cartridge was eluted with ether (20 mL). The eluate was evaporated to dryness and the residue was purified by preparative HPLC to afford (R)-methyl 1-(2-adamantylcarbamoyl)pyrrolidin-3-ylcarbamate (15 mg, 49%). LC-MS Method 1, tR=1.5 min, m/z=322; 1H NMR (CDCl3) 1.60-2.00 (15H), 2.20 (m, 1H), 3.26 (m, 1H), 3.46 (m, 2H), 3.63 (m, 1H), 3.69 (s, 3H), 3.96 (s, 1H), 4.30 (1H), 4.60 (1H), 4.89 (d, 1H).

Workup

  1. customA vial equipped with a flea
  2. stirringThe solution was stirred
  3. stirringThe mixture was stirred overnight at rt
  4. washThe cartridge was eluted with ether (20 mL)
  5. customThe eluate was evaporated to dryness
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-724df9aec2fb4fa3807f2ad05ffc022b
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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