Boron tribromide → HCID 178499347, compound

HRID 1614908Notes

Reaction equation

HRID 1614908 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

Conditions

Temperature
0 °C

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° C. was treated with boron tribromide (0.85 mL, 1.0 M solution in DCM). The mixture was stirred at 0° 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. customquenched with the addition of silica gel
  2. customVolatiles were evaporated under reduced pressure
  3. customthe reaction mixture was purified by silica gel chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-4a8e0b9d5fd5444b925d16d8fb18d055
Source dataset
uspto-grants-2014_07
Patent number
US08765722B2

Reaction notes

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