Hydrogen Bromide → (1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromide

HRID 1031587Notes

Reaction equation

HRID 1031587 reaction equation
[BrH:1].C1(C)C=CC(S([N:11]2[CH2:16][C@H:15]3[CH2:17][C@@H:12]2[CH2:13][N:14]3[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=O)=O)=CC=1>C(O)(=O)C>[BrH:1].[BrH:1].[C:19]1([CH2:18][N:14]2[CH2:13][C@H:12]3[CH2:17][C@@H:15]2[CH2:16][NH:11]3)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14612539(1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 14612541(1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromideYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a hot solution of 2.85 L of hydrobromic acid 33% in acetic acid* at 70° C. there was added 1428 g (4.17 moles) of (1R, 4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo-[2.2.1]-heptane (8). The solution was stirred for 12 h. The resulting suspension was cooled (18°-20° C.). The precipitate was filtered, washed with diisopropylether and dried at 40° C. under reduced pressure to give 1294 g (89%) of the titled compound. M.P. =276° C. [α]D =-0.38° (c=1, H2O).

Workup

  1. temperatureThe resulting suspension was cooled (18°-20° C.)
  2. filtrationThe precipitate was filtered
  3. washwashed with diisopropylether
  4. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-cc3d641c58ff497dbf65aeb380c5097b
Source dataset
uspto-grants-1990_09
Patent number
US04954507

Reaction notes

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