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

HRID 401784Notes

Reaction equation

HRID 401784 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-a8fe73e4a4a64a66ba50205ab1fe4722
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

Loading…