Hydrochloric Acid → (r)-6,8-Dibromochroman-4-amine hydrochloride

HRID 1008960Notes

Reaction equation

HRID 1008960 reaction equation
[N:1]([C@H:4]1[C:13]2[C:8](=[C:9]([Br:15])[CH:10]=[C:11]([Br:14])[CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+]=[N-].CP(C)C.[ClH:20]>O1CCCC1.C(#N)C>[ClH:20].[Br:14][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]([Br:15])[CH:10]=1)[O:7][CH2:6][CH2:5][C@H:4]2[NH2:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68983TrimethylphosphineHCID 866200164(R)-Azido-6,8-dibromo-chroman

Product 1

HCID 67303951(r)-6,8-Dibromochroman-4-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 4(R)-azido-6,8-dibromo-chroman in tetrahydrofuran (0.16M) was added 1.2 equivalents of trimethylphosphine. The mixture was warmed to room temperature and maintained for 16 h. Concentration of the mixture gave the crude amine. This was dissolved in acetonitrile (0.20M) and 2 equivalents of hydrochloric acid added. The mixture was stirred for 16 h and the solids filtered, washed with acetonitrile and dried to afford the title compound as an off-white solid.

Workup

  1. temperaturemaintained for 16 h
  2. customConcentration of the mixture gave the crude amine
  3. filtrationthe solids filtered
  4. washwashed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-54eb609add124280b639e552de9d8428
Source dataset
uspto-grants-2011_07
Patent number
US07973050B2

Reaction notes

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