Boron tribromide → HCID 57554654, compound

HRID 1511856Notes

Reaction equation

HRID 1511856 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:18][CH2:17][C@@:11]3([NH:15][C:14](=[O:16])[O:13][CH2:12]3)[CH2:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:18][CH2:17][C@@:11]3([NH:15][C:14](=[O:16])[O:13][CH2:12]3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57554655HCID 57554655, compound

Product 1

HCID 57554654HCID 57554654, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (5R,7R)-7-(4-methoxy-phenyl)-3-oxa-1-aza-spiro[4.4]nonan-2-one (3.95 g, 16.0 mmol) in DCM (30 mL) was cooled in an ice bath and 1M BBr3 in DCM solution (64.0 mL, 64.0 mmol) was added at a rapid dropwise rate and the reaction was allowed to continue stirring at about 0° C. for about 0.5 hour. The reaction was quenched by dropwise addition of methanol (25.0 mL). The reaction was allowed to warm to room temperature and then concentrated. The residue was triturated with water (50 mL), filtered, rinsed with water (2×5.0 mL), and dried to yield 3.14 g (84%) of (5R,7R)-7-(4-hydroxy-phenyl)-3-oxa-1-aza-spiro[4.4]nonan-2-one as a gray solid.

Workup

  1. customThe reaction was quenched by dropwise addition of methanol (25.0 mL)
  2. temperatureto warm to room temperature
  3. concentrationconcentrated
  4. customThe residue was triturated with water (50 mL)
  5. filtrationfiltered
  6. washrinsed with water (2×5.0 mL)
  7. customdried

Sources & evidence

ORD record
ord-b2957a54d73e40d6b5b5c0bb8a47f400
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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