1,1-Dimethylethyl 4-azido-1-piperidinecarboxylate → 4-[4-(4-Methanesulfonyl-phenoxymethyl)-[1,2,3]triazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1928600Notes

Reaction equation

HRID 1928600 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]=[N+:15]=[N-:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]#[CH:30])=[CH:23][CH:22]=1)(=[O:20])=[O:19].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.CC(O)(C)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:30]=[C:29]([CH2:28][O:27][C:24]3[CH:25]=[CH:26][C:21]([S:18]([CH3:17])(=[O:19])=[O:20])=[CH:22][CH:23]=3)[N:16]=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 114587941,1-Dimethylethyl 4-azido-1-piperidinecarboxylateHCID 23667548Sodium AscorbateHCID 577083901-(Methylsulfonyl)-4-(prop-2-ynyloxy)benzene

Product 1

HCID 251763634-[4-(4-Methanesulfonyl-phenoxymethyl)-[1,2,3]triazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

4-Azido-piperidine-1-carboxylic acid tert-butyl ester (1 eq) and 1-methanesulfonyl-4-prop-2-ynyloxy-benzene (1 eq) were suspended in H2O/t-BuOH (1:1). Sodium ascorbate (0.1 eq) was added followed by CuSO4.5H2O (0.01 eq). The mixture was stirred vigorously overnight. The mixture was diluted with water and a precipitate formed. The precipitate was collected by filtration and purified on silica gel to give the desired product. 1H NMR (CDCl3): δ 7.88 (2H, d), 7.67 (1H, s), 7.14 (2H, d), 5.29 (2H, s), 4.64 (1H, m), 4.28 92H, m), 3.05 (3H, s), 2.94 (2H, m), 2.2 (2H, m), 1.96 (2H, m), 1.48 (9H, s).

Workup

  1. customa precipitate formed
  2. filtrationThe precipitate was collected by filtration
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-f350b07817fb41c5806a8a0461c6ed62
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

Loading…