Triethyl phosphonoacetate → Ethyl azepan-3-ylacetate hydrochloride

HRID 550785Notes

Reaction equation

HRID 550785 reaction equation
[H-].[Na+].C(N1CCCCC(=O)C1)C1C=CC=CC=1.C(OP(CC(OCC)=O)(OCC)=O)C.C([N:39]1[CH2:45][CH2:44][CH2:43][CH2:42][C:41](=[CH:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:40]1)C1C=CC=CC=1.[ClH:52].CCOC(C)=O>[Pd].CCO.C1COCC1>[ClH:52].[NH:39]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]([CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:40]1

Participants

9

Reactant 5

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 151522641-Benzylazepan-3-oneHCID 21866389Hydrogen chloride-ethyl acetateHCID 86619134Ethyl(1-benzylazepane-3-ylidene)acetate

Product 1

HCID 67196857Ethyl azepan-3-ylacetate hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride and 1-benzylazepan-3-one were added to a THF solution of ethyl diethoxyphosphorylacetate with ice-cooling, and the mixture was stirred at ambient temperature for 2 hours to yield a stereoisomeric mixture of ethyl (1-benzylazepan-3-ylidene)acetate, which was treated with 4M HCl-EtOAc solution, followed by adding EtOH and 10% palladium on activated carbon and stirring under hydrogen atmosphere at ambient temperature for 15 hours to yield ethyl azepan-3-ylacetate hydrochloride.

Workup

  1. temperaturecooling
  2. customto yield
  3. stirringstirring under hydrogen atmosphere at ambient temperature for 15 hours

Sources & evidence

ORD record
ord-7dba38f338db40d7bb67d72c3cb339d2
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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