Methane → HCID 58092727, compound

HRID 1807667Notes

Reaction equation

HRID 1807667 reaction equation
C[Al](C)C.[Cl-].[NH4+:6].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.Cl>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]([NH2:6])=[O:9]

Participants

7

Reactant 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 66879352HCID 66879352, compound

Product 1

HCID 58092727HCID 58092727, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Trimethylaluminum in toluene (2 M, 3.23 mL) was added dropwise to a mixture of ammonium chloride (0.346 g, 6.47 mmol) in toluene (3.2 mL) at 0° C. under an argon atm., with the formation of methane gas. The RM was then allowed to warm to rt, and stirred at rt for a further 15 min. before (2S,3R)-3-methyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid methyl ester (prepared as described in Tetr. Lett. 1997, 38 (1), 85-88; 1.6 g, 6.47 mmol) was slowly added. The RM was stirred at it for 56 h, 1 M HCl was then added with cooling and the RM washed 3× with DCM. The aqueous phase was basified with Na2CO3, extracted 3× with DCM and the combined organic layers dried over Na2SO4. Evaporation gave the title compound as a yellowish oil. MS: M+H=233.2. HPLC: tR 3.17 min (method D). 1H-NMR (d6-DMSO, 600 MHz): 7.37-7.33 (m, 2H), 7.30 (t, 2H), 7.25 (s, br,1H), 7.21 (t, 1H), 7.12 (s, br,1H), 3.55 (q, 1H), 3.40 (d, 1H), 2.71 (t, 1H), 2.28-2.22 (m, 1H), 2.21-2.16 (m, 1H), 1.71 (qt, 1H), 1.38-1.31 (m, 1H), 1.21 (d, 3H), 0.90 (d, 3H).

Workup

  1. additionwas slowly added
  2. temperaturewith cooling
  3. washthe RM washed 3× with DCM
  4. extractionextracted 3× with DCM
  5. dry with materialthe combined organic layers dried over Na2SO4
  6. customEvaporation

Sources & evidence

ORD record
ord-5ade5da8430142b7851ce3a4934dc36b
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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