Triethyl phosphonoacetate → Ethyl azepan-3-ylacetate hydrochloride

HRID 225468Notes

Reaction equation

HRID 225468 reaction equation
[H-].[Na+].C(N1CCCCC(=O)C1)C1C=CC=CC=1.C(OP(CC(OCC)=O)(OCC)=O)C.[CH2:32]([O:34][C:35](=[O:51])[CH:36]=[C:37]1[CH2:43][CH2:42][CH2:41][CH2:40][N:39](CC2C=CC=CC=2)[CH2:38]1)[CH3:33].[ClH:52].CCOC(C)=O.[H][H]>[C].[Pd].CCO.C1COCC1>[ClH:52].[NH:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH:37]([CH2:36][C:35]([O:34][CH2:32][CH3:33])=[O:51])[CH2:38]1

Participants

10

Reactant 6

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 151522641-Benzylazepan-3-oneHCID 21866389Hydrogen chloride-ethyl acetateHCID 86619134Ethyl(1-benzylazepane-3-ylidene)acetate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 67196857Ethyl azepan-3-ylacetate hydrochloride

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride and 1-benzylazepane-3-one were added to a THF solution of ethyl diethoxyphosphorylacetate under ice cooling and stirred for two hours at room temperature to give a stereoisomeric mixture of ethyl(1-benzylazepane-3-ylidene)acetate. After the obtained stereoisomeric mixture of ethyl(1-benzylazepane-3-ylidene)acetate was processed with 4M HCl-EtOAc solution, EtOH and 10% palladium carbon were added and stirred for 15 hours at room temperature under the hydrogen atmosphere to give ethyl azepane-3-ylacetate hydrochloride.

Workup

  1. customto give
  2. additionwere added

Sources & evidence

ORD record
ord-558f13f39a3c4606846a96222559fbfa
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

Loading…