Methanol → HCID 67713852, compound

HRID 1451506Notes

Reaction equation

HRID 1451506 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])[CH3:2].[Cl:28][Si](C)(C)C.CO>C1(C)C=CC=CC=1>[ClH:28].[ClH:28].[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][N:17]([CH2:24][CH:25]([CH3:26])[CH3:27])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 53985595HCID 53985595, compound

Product 1

HCID 67713852HCID 67713852, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of the above ester (8.0 g, 21 mmol) in anhydrous toluene (30 ml) was added a solution of chlorotrimethylsilane (4.6 g, 42 mmol) in anhydrous toluene (10 ml). Methanol (1.7 ml, 42 mmol) was carefully added and the resulting mixture left for crystallisation to give 6.2 g of (R)-1-(2-(2-(N-(2-methyl-1-propyl)-N-phenylamino)ethoxy)ethyl)-3-piperidinecarboxylic acid ethyl ester dihydrochloride.

Workup

  1. waitthe resulting mixture left for crystallisation

Sources & evidence

ORD record
ord-63a490021edb4aceaa3e5490f46fddf8
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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