Hydrochloric Acid → 7-(Hydroxymethyl)azepan-2-one

HRID 1710394Notes

Reaction equation

HRID 1710394 reaction equation
C([O:3][C:4]([CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8](=[O:13])[NH:7]1)=O)C.B.[Li].Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O1CCCC1>[OH:3][CH2:4][CH:6]1[NH:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12371765Ethyl 7-oxoazepane-2-carboxylateHCID 178419226HCID 178419226, compound

Product 1

HCID 214467037-(Hydroxymethyl)azepan-2-oneYield 60.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.10 g of 7-oxo-azepane-2-carboxylic acid ethyl ester (compound G1) are dissolved in 150 ml of dichloromethane under an atmosphere of dry nitrogen. At room temperature, 8.45 ml of lithium boron hydride solution in tetrahydrofuran (strength 2.0 M) are slowly added to the solution in the course of 10 min. Thereafter, the reaction mixture is stirred for 17 hours overnight at room temperature. Subsequently, the mixture is cooled in an ice bath and acidified to pH 1 using hydrochloric acid (strength 3.0 M). Under stirring, the reaction mixture is allowed to warm up to room temperature. Thereafter, potassium carbonate is carefully added thereby re-adjusting neutral pH. The reaction mixture is filtered with suction and the filtrate is concentrated in vacuo. Purification is achieved by flash chromatography (eluent gradient: dichloromethane/0-10 vol. % ethanol) to yield 1.46 g of the title compound as colorless solid of m.p. 100° C. ESI-MS: 144.1 (MH+). TLC: Rf=0.47 (dichloromethane/ethanol 10:1 parts by volume; iodine staining).

Workup

  1. temperatureSubsequently, the mixture is cooled in an ice bath
  2. stirringUnder stirring
  3. temperatureto warm up to room temperature
  4. filtrationThe reaction mixture is filtered with suction
  5. concentrationthe filtrate is concentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-6b686023a7dc4834a1c62be43cd90577
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

Loading…