Methane → HCID 58092727, compound

HRID 2066788Notes

Reaction equation

HRID 2066788 reaction equation
C[Al](C)C.[NH4+:5].[Cl-].C.C[O:9][C:10]([C@@H:12]1[C@H:16]([CH3:17])[CH2:15][CH2:14][N:13]1[C@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])=O>C1(C)C=CC=CC=1>[CH3:17][C@@H:16]1[CH2:15][CH2:14][N:13]([C@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[C@@H:12]1[C:10]([NH2:5])=[O:9]

Participants

6

Reactant 4

HCID 297MethaneHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 66879352HCID 66879352, compound

Product 1

HCID 58092727HCID 58092727, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Trimethylaluminum in toluene (2 M, 6.46 mmol) was added dropwise to a mixture of NH4Cl (6.47 mmol) in toluene (3.2 mL) at 0° C. with the formation of methane gas. The reaction mixture was allowed to warm to rt, stirred for a further 15 min and then slowly treated with (2S,3R)-3-methyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid methyl ester (prepared as described in Tet. Lett. 1997, 38, 85-88) (6.47 mmol). After stirring for 56 h, the mixture was cooled to 0° C., quenched with 1M HCl and then washed with CH2Cl2 (3×). The aqueous phase was basified with a saturated solution of NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a colorless oil. ESI-MS: [M+H]+ 233; HPLC: tR 2.35 min (method A).

Workup

  1. stirringAfter stirring for 56 h
  2. temperaturethe mixture was cooled to 0° C.
  3. customquenched with 1M HCl
  4. washwashed with CH2Cl2 (3×)
  5. extractionextracted with CH2Cl2 (3×)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified

Sources & evidence

ORD record
ord-441337dad46c44a0a8da6c4ab1f0835d
Source dataset
uspto-grants-2012_10
Patent number
US08293753B2

Reaction notes

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