Water → HCID 24851751, compound

HRID 1015571Notes

Reaction equation

HRID 1015571 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:29][CH:14]4[CH2:15][C:16]([NH:18][CH2:19][C:20]([N:22]5[CH2:26][CH2:25][CH2:24][C@H:23]5[C:27]#[N:28])=[O:21])([CH2:17]2)[CH:12]([CH2:13]4)[CH2:11]3)=[CH:6][CH:5]=1)([O-])=O.O.C1COCC1.[NH4+].[Cl-]>[Fe].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]23[CH2:29][CH:14]4[CH2:15][C:16]([NH:18][CH2:19][C:20]([N:22]5[CH2:26][CH2:25][CH2:24][C@H:23]5[C:27]#[N:28])=[O:21])([CH2:17]2)[CH:12]([CH2:13]4)[CH2:11]3)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 24853442HCID 24853442, compound

Product 1

HCID 24851751HCID 24851751, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of the compound obtained from example 29 (0.2 g, 0.51 mmol) in a 1:2:4 mixture of water, THF, and ethanol (7 mL) respectively was sequentially added solid NH4Cl (0.1 g, 1.87 mmol) and Fe powder (0.1 g, 1.78 mmol). The reaction mixture was heated to reflux for 2 h. After cooling the reaction mixture to room temperature, it was filtered through a small pad of celite and washed the bed with EtOAc. The filtrate was evaporated under reduced pressure and the residue was diluted with water and extracted with EtOAc. The combined organic layer was washed with water, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to obtain (2S)-1-{N-[2-(4-aminophenyl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile as off-white solid (0.09 g) in 50% yield. m/z (M+1) 365; 1H NMR (CDCl3) 300 MHz δ 7.05 (d, J=8.5 Hz, 2H), 6.63 (d, J=8.5 Hz, 2H), 4.90-4.75 (m, 1H), 3.80-3.40 (m, 4H), 2.45-1.70 (m, 15H), 1.65-1.57 (m, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationit was filtered through a small pad of celite
  4. washwashed the bed with EtOAc
  5. customThe filtrate was evaporated under reduced pressure
  6. additionthe residue was diluted with water
  7. extractionextracted with EtOAc
  8. washThe combined organic layer was washed with water
  9. dry with materialdried over anhydrous Na2SO4
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ee396f85e17b4f08b0de3a639584e88d
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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