Hydrogen Bromide → HCID 89813315, compound

HRID 1051873Notes

Reaction equation

HRID 1051873 reaction equation
[BrH:1].[CH2:2]1[C:4]2([CH2:9][CH2:8][CH2:7][N:6](C(OCC3C=CC=CC=3)=O)[CH2:5]2)[CH2:3]1>CCCCCC>[BrH:1].[CH2:3]1[C:4]2([CH2:9][CH2:8][CH2:7][NH:6][CH2:5]2)[CH2:2]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 898132135-Azaspiro[2.5]octane-5-carboxylic acid, phenylmethyl ester2×

Product 1

HCID 89813315HCID 89813315, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

HBr (6.16 g, 4.13 ml, 30% solution in glacial acetic acid, 22.83 mmol) was added to a benzyl 5-azaspiro[2.5]octane-5-carboxylate (step 1 of intermediate 3, 2.8 g, 11.41 mmol) at 0° C. Reaction mixture was stirred at 25° C. for 3 hr. The progress of reaction was monitored by TLC. Reaction mixture was diluted with hexane (25 ml) and stirred for 15 min at 25° C. Organic layer was separated and solid was again stirred with diethyl ether (25 ml). Solvent layer was removed by decanting and solid was dried to obtain the title compound (1.86 g, 85%). MS: m/z 112 (M+1).

Workup

  1. customReaction mixture
  2. customThe progress of reaction
  3. customReaction mixture
  4. stirringstirred for 15 min at 25° C
  5. customOrganic layer was separated
  6. stirringsolid was again stirred with diethyl ether (25 ml)
  7. customSolvent layer was removed
  8. customby decanting
  9. customsolid was dried

Sources & evidence

ORD record
ord-8e5929f57d23441fa3b66e6c6f475b40
Source dataset
uspto-grants-2016_07
Patent number
US09388196B2

Reaction notes

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