Methylamine → (S)-tert-butyl 4-((R)-5-tert-butoxy-2-((methylamino)methyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 451811Notes

Reaction equation

HRID 451811 reaction equation
[C:1]([O:5][C:6](=[O:37])[CH2:7][CH2:8][C@@H:9]([CH2:25]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:10][C@H:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:4])([CH3:3])[CH3:2].[CH3:38][NH2:39]>CCO>[C:1]([O:5][C:6](=[O:37])[CH2:7][CH2:8][C@@H:9]([CH2:25][NH:39][CH3:38])[CH2:10][C@H:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59201330(S)-tert-butyl 4-((R)-5-tert-butoxy-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59201399(S)-tert-butyl 4-((R)-5-tert-butoxy-2-((methylamino)methyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(S)-tert-butyl 4-((R)-5-tert-butoxy-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (300 mg, 0.55 mmol) was dissolved in 30% MeNH2 in EtOH (60 mL), the solution was heated to 70° C. for 2 h in a pressure sealed vessel. After cooling to rt, the solvent was removed under reduced pressure to give (S)-tert-butyl 4-((R)-5-tert-butoxy-2-((methylamino)methyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate (212 mg, 95%). MS ESI +ve m/z 401 (M+H).

Workup

  1. customsealed vessel
  2. temperatureAfter cooling to rt
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3c36ef59a7104325b6b6f899fd7d050b
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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