2-Methylbutylamine → HCID 9924392, compound

HRID 636655Notes

Reaction equation

HRID 636655 reaction equation
[CH3:1][CH:2]([CH2:5][CH3:6])[CH2:3][NH2:4].C(N(CC)CC)C.Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl.[NH:26]1[CH2:30][CH2:29][CH2:28][C@H:27]1[C:31]([O:33][CH2:34][CH2:35][CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)=[O:32]>C(Cl)Cl>[CH3:1][CH:2]([CH2:5][CH3:6])[CH2:3][NH:4][C:15]([N:26]1[CH2:30][CH2:29][CH2:28][C@H:27]1[C:31]([O:33][CH2:34][CH2:35][CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)=[O:32])=[O:17]

Participants

6

Reactant 4

HCID 72832-MethylbutylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 15427667HCID 15427667, compound

Product 1

HCID 9924392HCID 9924392, compoundYield 167.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2-methylbutylamine (113 mg; 1.3 mmol) and triethylamine (132 mg; 1.3 mmol) in methylene chloride (5 mL) was added to a solution of triphosgene (128 mg; 0.43 mmol) in methylene chloride (5 mL). The resulting mixture was refluxed for 1 hour and then cooled to room temperature. 3-(3-Pyridyl)-1-propyl (2S)-pyrrolidine-2-carboxylate (300 mg; 1.3 mmol) in 5 mL of methylene chloride was added and the resulting mixture was stirred for 1 hour and then partitioned between water and a 1:1 mixture of ethyl acetate and hexane. The organic phase was dried, concentrated and purified by column chromatography (50% ethyl acetate/hexane) to obtain 250 mg (55%) of the compound of Example 1 (Compound 1, Table I) as an oil. 1H NMR (CDCl3, 300 MHz): δ 0.89-0.93 (m, 6H); 1.10-1.20 (m, 1H); 1.27 (s, 1H); 1.36-1.60 (m, 2H); 1.72 (s, 2H); 1.97-2.28 (m, 6H); 2.70-2.75 (m, 2H); 2.92-3.54 (m, 4H); 4.16-4.20 (dt, 2H); 4.45-4.47 (m, 2H); 7.21-7.29 (m, 1H); 7.53-7.56 (dd, 1H); 8.46-8.48 (s, 2H). Analysis calculated for C19H29N3O3—0.5 H2O: C, 64.02; H, 8.48; N, 11.79. Found: C, 63.72; H, 8.42; N, 11.83.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 hour
  2. custompartitioned between water
  3. additiona 1:1 mixture of ethyl acetate and hexane
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-93f2a2402fcd4a13814bd788ee74b463
Source dataset
uspto-grants-2001_02
Patent number
US06194440B1

Reaction notes

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