Benzyl Alcohol → Benzyl azepane-3-carboxylate

HRID 647449Notes

Reaction equation

HRID 647449 reaction equation
[C:1]([CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][CH2:5]1)([OH:3])=[O:2].S(Cl)(Cl)=O.CCOCC.[CH2:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([O:2][C:1]([CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][CH2:5]1)=[O:3])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 13457776Azepane-3-carboxylic acid

Product 1

HCID 13457777Benzyl azepane-3-carboxylate

Procedure

Suspend 1.15 g of 3-carboxyperhydroazepine [P. Krogsgaard-Larsen et al., Acta Chem. Scand., B32, 327 (1978)] in 8 ml benzyl alcohol. Cool the mixture to 0° and add 1 ml thionyl chloride. Stir the mixture at room temperature for 48 hours, then add it dropwise to 300 ml ether with vigorous stirring. Decant the ether and dissolve the residue in H2O. Wash the aqueous solution with ether, then make it to pH 12 and extract with ethyl acetate. Dry the extracts and concentrate in vacuo to obtain 3-benzyloxycarbonylperhydroazepine.

Workup

  1. temperatureCool the mixture to 0°
  2. customDecant the ether
  3. dissolutiondissolve the residue in H2O
  4. washWash the aqueous solution with ether
  5. extractionextract with ethyl acetate
  6. customDry the extracts
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-fe82fb097b73436da5601e2b11045de5
Source dataset
uspto-grants-1983_10
Patent number
US04409146

Reaction notes

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