Boron tribromide → HCID 67432092, compound

HRID 454977Notes

Reaction equation

HRID 454977 reaction equation
[OH:1][CH2:2][C@H:3]([NH:12][C:13]([C@H:15]1[CH2:17][C@@H:16]1[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10]C)=[CH:6][CH:5]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl>[OH:1][CH2:2][C@H:3]([NH:12][C:13]([C@H:15]1[CH2:17][C@@H:16]1[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 67432195HCID 67432195, compoundHCID 129711818HCID 129711818, compound

Product 1

HCID 67432092HCID 67432092, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-7.5 °C

Procedure

To a suspension of (1S,2S)-2-thiophen-2-yl-cyclopropanecarboxylic acid [(R)-2-hydroxy-1-(4-methoxy-phenyl)-ethyl]-amide (105 mg, 0.331 mmol) in DCM (3 mL) at −10° C. was added BBr3 (1M, 0.994 mL, 0.994 mmol). The mixture was stirred between −10 to −5° C. for 1 h. Work up with NaHCO3/HCl to give the crude product which was further purified by flash column (5% MeOH in DCM) of give the titled product (70 mg, 70%).

Workup

  1. customto give the crude product which
  2. customwas further purified by flash column (5% MeOH in DCM)

Sources & evidence

ORD record
ord-cdff5961951d452c906dbf946cd45285
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

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