benzyl 2-((R)-5-(2H-1,2,3-triazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate → 2-((R)-5-[1,2,3]triazol-2-yl-indan-1-yl)-2,7-diaza-spiro[3.5]nonane

HRID 1913462Notes

Reaction equation

HRID 1913462 reaction equation
[N:1]1[N:2]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[C@H:11]([N:15]2[CH2:18][C:17]4([CH2:23][CH2:22][N:21](C(OCC5C=CC=CC=5)=O)[CH2:20][CH2:19]4)[CH2:16]2)[CH2:10][CH2:9]3)[N:3]=[CH:4][CH:5]=1>CO.[Pd]>[N:1]1[N:2]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[C@H:11]([N:15]2[CH2:16][C:17]4([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[CH2:18]2)[CH2:10][CH2:9]3)[N:3]=[CH:4][CH:5]=1

Participants

4

Reactant 1

HCID 58438480benzyl 2-((R)-5-(2H-1,2,3-triazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 584384932-((R)-5-[1,2,3]triazol-2-yl-indan-1-yl)-2,7-diaza-spiro[3.5]nonane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a Parr® shaker bottle, a solution of benzyl 2-(R)-5-(2H-1,2,3-triazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate (6-1b, 1.20 g, 2.7 mmol) in MeOH (30 mL) was treated with 10% Pd/C (50% wet for safety, 600 mg). The mixture was hydrogenated at 45 psi for 6 hours. The reaction was filtered through a pad of Celite® and concentrated to afford 2-((R)-5-(2H-1,2,3-triazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane as a glass-like solid (690 mg, 82%). MS (ES+) 310.0 (M+H)+. 1H NMR (CD3OD) δ 0.95 (s, 1H), 1.27-1.32 (m 2H), 1.88-1.92 (m, 3H), 2.26-2.30 (m, 1H), 2.97-3.01 (m, 5H), 3.13 (s, 3H), 3.33-3.51 (m, 1H), 4.07 (br s, 1H), 7.50 (s, 2H), 7.90 (s, 3H).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-af3a7c773d674f21ab89b4bb056f35e9
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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