Boron tribromide → HCID 178499347, compound

HRID 1046405Notes

Reaction equation

HRID 1046405 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:32]#[C:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:23][C@@H:22]([O:24]CC2C=CC=CC=2)[CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:32]#[C:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:23][C@@H:22]([OH:24])[CH2:21]1)[C:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178499348HCID 178499348, compound

Product 1

HCID 178499347HCID 178499347, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[(cis-3-benzyloxy-cyclobutyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (290 mg, 0.55 mmol) in DCM (2 mL) at 0 deg C. was treated with boron tribromide (0.85 mL, 1.0 M solution in DCM). The mixture was stirred at 0 deg C. for 15 minutes and quenched with the addition of silica gel. Volatiles were evaporated under reduced pressure and the reaction mixture was purified by silica gel chromatography (0-100% ethyl acetate:hexanes). This resulted in 210 mg (88% yield) of 5-(3,3-Dimethyl-but-1-ynyl)-3-[(cis-3-hydroxy-cyclobutyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester.

Workup

  1. customat 0 deg C
  2. customquenched with the addition of silica gel
  3. customVolatiles were evaporated under reduced pressure
  4. customthe reaction mixture was purified by silica gel chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-44e1c573920c496b850aa746f31ff399
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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