Hydrochloric Acid → HCID 94236821, compound

HRID 1507199Notes

Reaction equation

HRID 1507199 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:9]1=[O:24])(C)(C)C.Cl>O1CCOCC1>[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:9]1=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118221098HCID 118221098, compound

Product 1

HCID 94236821HCID 94236821, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 0° C. solution of (R)-tert-butyl(1-(3,4-dimethoxybenzyl)-2-oxopyrrolidin-3-yl)carbamate (0.7 g, 2 mmol) in dioxane (2 mL) was added dropwise HCl (1 mL, 12 mmol). The solution was allowed to warm up to RT with stirring over 2 h. It was then concentrated under vacuum and the residue was triturated with diethyl ether. Yield 400 mg crude (R)-3-amino-1-(3,4-dimethoxybenzyl)-pyrrolidin-2-one. LCMS (Method J) RT 0.5 min, m/z 251.1 (MH+), 1H NMR (400 MHz, chloroform-d) δ 2.48 (br s, 4H), 3.35 (br s, 2H), 3.70 (s, 3H), 3.8-3.95 (m, 6H), 4.4 (br s, 3H), 6.76 (br s, 3H), 8.81 (br s, 3H).

Workup

  1. concentrationIt was then concentrated under vacuum
  2. customthe residue was triturated with diethyl ether
  3. customLCMS (Method J) RT 0.5 min, m/z 251.1 (MH+), 1H NMR (400 MHz, chloroform-d) δ 2.48 (br s, 4H), 3.35 (br s, 2H), 3.70 (s, 3H), 3.8-3.95 (m, 6H), 4.4 (br s, 3H), 6.76 (br s, 3H), 8.81 (br s, 3H)

Sources & evidence

ORD record
ord-9f14ef2e044f4a7a81c3595560ca0589
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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