Hydrochloric Acid → (2R,3R)-3-methoxy-2-methyl-N-(2-phenylethyl)-3-[(2S)-pyrrolidin-2-yl] propanamide, hydrochloride salt

HRID 74731Notes

Reaction equation

HRID 74731 reaction equation
[CH3:1][O:2][C@@H:3]([C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1C(OC(C)(C)C)=O)[C@@H:4]([CH3:16])[C:5](=[O:15])[NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[ClH:29]>O1CCOCC1.CO>[ClH:29].[CH3:1][O:2][C@@H:3]([C@@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1)[C@@H:4]([CH3:16])[C:5]([NH:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86685721tert-butyl (2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[(2-phenylethyl)amino]propyl}pyrrolidine-1-carboxylate

Product 1

HCID 131731845(2R,3R)-3-methoxy-2-methyl-N-(2-phenylethyl)-3-[(2S)-pyrrolidin-2-yl] propanamide, hydrochloride salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To #20 (7.00 g, 17.9 mmol, 1 eq.) in dioxane (50 mL, 0.36 M) and methanol (2 mL) was added a 4 M solution of hydrochloric acid in dioxane (20 mL, 80 mmol, 4.4 eq.). After stirring for 18 hours, the mixture was concentrated to afford #24 (5.86 g, quantitative) as a gum, which was used without further purification; LC-MS: 292.2 [M+H+], retention time=0.47 minutes.

Workup

  1. concentrationthe mixture was concentrated
  2. customto afford #24 (5.86 g, quantitative) as a gum, which
  3. customwas used without further purification

Sources & evidence

ORD record
ord-7cf5dbdfc70c4915b53275b67a300a2f
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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