Formic Acid → HCID 77506424, compound

HRID 1176242Notes

Reaction equation

HRID 1176242 reaction equation
C(O)=O.[CH3:4][O:5][C:6]1[CH:53]=[CH:52][CH:51]=[CH:50][C:7]=1[CH2:8][O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]2[O:33][CH2:34][C:35]2[O:36][C:37]3[C:43]([O:44][CH2:45][CH2:46][CH2:47][O:48][CH3:49])=[CH:42][CH:41]=[CH:40][C:38]=3[CH:39]=2)=[CH:16][CH:15]=1.C(N(CC)CC)C>CC(C)=O.[Pd]>[CH3:4][O:5][C:6]1[CH:53]=[CH:52][CH:51]=[CH:50][C:7]=1[CH2:8][O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]2[O:33][CH2:34][CH:35]2[CH2:39][C:38]3[CH:40]=[CH:41][CH:42]=[C:43]([O:44][CH2:45][CH2:46][CH2:47][O:48][CH3:49])[C:37]=3[O:36]2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 68571657HCID 68571657, compound

Product 1

HCID 77506424HCID 77506424, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

0.035 ml of formic acid are added to the suspension of 0.20 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[7-(3-methoxypropoxy)benzofuran-2-ylmethoxy]piperidine-1-carboxylate (Example 7a) and 0.20 g of 10% Pd/C in 3 ml of acetone. After 15 minutes, 0.16 ml of triethylamine is added in portions. The reaction mixture is stirred at room temperature over 20 hours and clarified by filtration, and the filtrate is concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.34 (1:2 EtOAc-heptane); Rt=6.24.

Workup

  1. filtrationclarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-bdcf7c4bcb7d487483577296322222a8
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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