Dimethylformamide → HCID 10861009, compound

HRID 1795165Notes

Reaction equation

HRID 1795165 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)([CH2:14]OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=[CH:29][N:28]=[N:27]1.[Na].[CH3:32][N:33](C)C=O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)([CH2:14][N:28]2[CH:29]=[N:33][CH:32]=[N:27]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 22228407HCID 22228407, compoundHCID 178507080HCID 178507080, compound

Product 1

HCID 10861009HCID 10861009, compoundYield 79.7%

Conditions

Temperature
100 °C

Procedure

To a solution of 4-cyclohexyl-4-methansulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (39 g, 103.8 mmol) in N,N-dimethylformamide (200 mL) is added sodium triazole (38 g, 415.2 mmol). The resulting solution is heated to 100° C. for 24 hours then cooled to room temperature. The solvent is removed under reduce pressure and the crude product purified over silica (80:20 EtOAc:hexane) to afford 28.7 g (79.7% yield) of the desired compound as a colorless solid. 1H NMR (CD3OD) δ 0.95–1.90 (m, 15H), 1.46 (s, 9H), 3.45–3.55 (m, 4H), 4.34 (s, 2H), 7.99 (s, 1H), 8.48 (s, 1H). MS (ESI) m/z 349, (M+H+), 371(M+Na+)

Workup

  1. temperaturethen cooled to room temperature
  2. customThe solvent is removed
  3. customthe crude product purified over silica (80:20 EtOAc:hexane)

Sources & evidence

ORD record
ord-7f586c76d7b442a0b45b90c530a4639b
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

Loading…