Methanol → (S)-6-(4-bromophenyl)-1,4-oxazepane hydrochloride

HRID 515464Notes

Reaction equation

HRID 515464 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:14][O:13][CH2:12][CH2:11][N:10]([C@@H](C3C=CC=CC=3)C)[CH2:9]2)=[CH:4][CH:3]=1.[Cl:23]C(OC(Cl)C)=O.CO>ClCCCl>[ClH:23].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:14][O:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 67281235(S)-6-(4-bromophenyl)-4-((R)-1-phenylethyl)-[1,4]oxazepane

Product 1

HCID 66718622(S)-6-(4-bromophenyl)-1,4-oxazepane hydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (S)-6-(4-bromophenyl)-4-((R)-1-phenylethyl)-[1,4]oxazepane (0.610 g, 1.69 mmol) in 1,2-dichloroethane (2.83 ml) was added 1-chloroethyl chloroformate (0.605 g, 4.23 mmol) at room temperature. The mixture was refluxed for 4 hours and cooled to room temperature. After addition of methanol (5.0 ml), the mixture was refluxed for 3 hours and concentrated under reduced pressure to afford the crude product. This crude product was washed with ether, dried under reduced pressure to afford (S)-6-(4-bromophenyl)-1,4-oxazepane hydrochloride as white solid (0.424 g, 86%).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturethe mixture was refluxed for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. washThis crude product was washed with ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e4d26c374edc467098608dcbc572e5a1
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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