1,4-Dioxane hydrochloride → 6-Benzyl-1,4-oxazepan-6-ol hydrochloride

HRID 401816Notes

Reaction equation

HRID 401816 reaction equation
[CH2:1]([C:8]1([OH:22])[CH2:14][O:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:23].O1CCOCC1>O1CCOCC1>[ClH:23].[CH2:1]([C:8]1([OH:22])[CH2:14][O:13][CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57732098tert-Butyl 6-benzyl-6-hydroxy-1,4-oxazepane-4-carboxylate

Product 1

HCID 685351506-Benzyl-1,4-oxazepan-6-ol hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 6-benzyl-6-hydroxy-1,4-oxazepane-4-carboxylate (Preparation 81, 37.15 g, 0.12 mol, 1 eq) was dissolved in dioxane (200 mL), and 4M hydrogen chloride/dioxane (60.4 mL, 0.24 mol, 2 eq) was added. The mixture was stirred for 24 h, evaporated, and coevaporated with ether. The formed precipitate was washed with ether and dried to title compound (27.3 g, 0.11 mol, 93%).

Workup

  1. customevaporated
  2. washThe formed precipitate was washed with ether

Sources & evidence

ORD record
ord-03c81aaf72e24e998f92f59c32cf7365
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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