1,4-Dioxane hydrochloride → 6-(2-Fluorobenzyl)-1,4-oxazepan-6-ol Hydrochloride

HRID 1808205Notes

Reaction equation

HRID 1808205 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][C:5]1([OH:19])[CH2:11][O:10][CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1.[ClH:24].O1CCOCC1>O1CCOCC1>[ClH:24].[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][C:5]1([OH:19])[CH2:11][O:10][CH2:9][CH2:8][NH:7][CH2:6]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57731942tert-Butyl 6-(2-fluorobenzyl)-6-hydroxy-1,4-oxazepane-4-carboxylate

Product 1

HCID 685346716-(2-Fluorobenzyl)-1,4-oxazepan-6-ol HydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 6-(2-fluorobenzyl)-6-hydroxy-1,4-oxazepane-4-carboxylate (Preparation 45, 38 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 give title compound (29.8 g, 0.11 mol, 95%).

Workup

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

Sources & evidence

ORD record
ord-0abe11a47c6e4ebd98a495c79d0e290a
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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