Water → HCID 89907390, compound

HRID 2271309Notes

Reaction equation

HRID 2271309 reaction equation
[O:1]=[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:5]2[CH:14]=[CH:15][CH2:16][CH:4]2[CH2:3]1.C(O[CH:22](N(C)C)[N:23]([CH3:25])[CH3:24])(C)(C)C.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:10]([O:9][C:7]([N:6]1[C:2](=[O:1])[C:3](=[CH:22][N:23]([CH3:25])[CH3:24])[CH:4]2[CH2:16][CH:15]=[CH:14][CH:5]12)=[O:8])([CH3:12])([CH3:13])[CH3:11]

Participants

6

Reactant 3

HCID 962WaterHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 68765962HCID 68765962, compound

Product 1

HCID 89907390HCID 89907390, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of tert-butyl 2-oxo-3,3a,4,6a-tetrahydrocyclopenta[b]pyrrole-1-carboxylate IV-1 (500 mg, 2.23 mmol) in toluene (11 mL) was added tert-butoxybis(dimethylamino)methane (1.39 mL, 6.71 mmol) The solution was heated for 2 h at 110° C. It was then cooled to room temperature, poured into water (20 mL), diluted with ethyl acetate (20 mL), and extracted 3 times. The combined organic layers were washed with brine, dried, concentrated and purified by flash chromatography (5% MeOH in CH2Cl2) giving the desired compound as a brown solid (367 mg, 58%); 1H NMR (400 MHz, CDCl3) 7.12 (1H, s), 5.99 (1H, m), 5.85 (1H, m), 4.91 (1H, d), 3.70 (1H, m), 3.03 (6H, s), 2.79 (1H, m), 2.40 (1H, dd), 1.54 (9H, s); LCMS (Method A): 0.83 min; ES+279 (M+H+).

Workup

  1. temperatureIt was then cooled to room temperature
  2. extractionextracted 3 times
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by flash chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-60203926175545d8aa4c8184c44eb8db
Source dataset
uspto-grants-2015_09
Patent number
US09119398B2

Reaction notes

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