3-Methyl-1-(5-nitro-pyridin-2-ylmethyl)azetidin-3-ol → 1-(5-Amino-pyridin-2-ylmethyl)-3-methyl-azetidin-3-ol

HRID 55890Notes

Reaction equation

HRID 55890 reaction equation
[CH3:1][C:2]1([OH:16])[CH2:5][N:4]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=2)[CH2:3]1>CO.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][N:4]2[CH2:3][C:2]([CH3:1])([OH:16])[CH2:5]2)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 903591743-Methyl-1-(5-nitro-pyridin-2-ylmethyl)azetidin-3-ol

Product 1

HCID 903566831-(5-Amino-pyridin-2-ylmethyl)-3-methyl-azetidin-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 53 (0.35 g, 2.2 mmol) in MeOH (6 mL) was added 10% Pd/C (50 mg) and hydrogenated using a balloon for 2 h at rt. The reaction mixture was filtered through a pad of Celite and concentrated to give the desired amine A4-18 (0.3 g, 69%) as a gummy liquid. Rf: 0.1 (10% MeOH/DCM); (m/z): 194 [MH]+; 1H NMR (400 MHz, DMSO-d6): δ 7.82 (1H, d, J=2.8 Hz), 6.95 (1H, d, J=8.4 Hz), 6.86 (1H, dd, J=8.4, 2.4 Hz), 5.12-5.10 (2H, m), 4.08 (1H, br s), 3.48 (2H, s), 3.16-3.14 (4H, m), 1.33 (3H, s).

Workup

  1. customfor 2 h
  2. customat rt
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2129e5cb23bd41e483995dbde2f20eb7
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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