Ammonium Hydroxide → (3R)-1-[3-(aminomethyl)phenyl]pyrrolidin-3-ol

HRID 2239334Notes

Reaction equation

HRID 2239334 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[CH2:3]1.[NH4+].[OH-]>[Rh].CCO>[NH2:11][CH2:10][C:9]1[CH:8]=[C:7]([N:4]2[CH2:5][CH2:6][C@@H:2]([OH:1])[CH2:3]2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 687092993-[(3R)-3-Hydroxypyrrolidin-1-yl]benzonitrile

Product 1

HCID 57601102(3R)-1-[3-(aminomethyl)phenyl]pyrrolidin-3-olYield 871.6%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalyst2×HCID 702EthanolSolvent

Procedure

To 3-[(3R)-3-hydroxypyrrolidin-1-yl]benzonitrile (0.070 g, 0.37 mmol) and 5% rhodium on alumina (15 mg) in abs EtOH (5 mL) was added NH4OH (26%, 1 mL). The resulting mixture was stirred under H2 over night. A second portion of 5% rhodium on alumina (30 mg) was added and the stirring under H2 continued for 2 days. The mixture was filtered through Celite and concentrated to give 0.62 g (69%) of the title compound (purity ˜80%). 1H NMR (400 MHz, CD3OD) δ 7.10 (dd, 1H, J=8.1, 7.6 Hz), 6.56 (d, 1H, J=7.6 Hz), 6.51 (s, 1H), 6.42 (dd, 1H, J=8.1, 2.0 Hz), 4.47 (m, 1H), 3.69 (s, 1H), 3.47-3.36 (m, 2H), 3.32-3.24 (m, 1H), 3.17 (bd, 1H, J=9-7 Hz), 2.15-1.93 (m, 2H). 13C NMR (MeOH-d4) δ 149.7, 143.4, 130.3, 115.8, 111.8, 111.7, 71.7, 57.0, 46.9, 46.7, 34.9.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bba8d3d985eb472cbe626192c2c53602
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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