Boron tribromide → HCID 51001654, compound

HRID 2381188Notes

Reaction equation

HRID 2381188 reaction equation
C[O:2][CH2:3][CH2:4][C@H:5]([C:32]([F:35])([F:34])[F:33])[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[O:15])=[CH:9][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][CH2:3][CH2:4][C@H:5]([C:32]([F:34])([F:35])[F:33])[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[O:15])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 51001655HCID 51001655, compound2×

Product 1

HCID 51001654HCID 51001654, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(Toluene-4-sulfonyl)-piperidine-4-carboxylic acid [4-((R)-3-methoxy-1-trifluoromethyl-propoxy)-phenyl]-amide (0.105 g), product of example 59), in methylene chloride (2 ml) was treated at RT and under an argon atmosphere with BBr3 (0.5 molar, 1 ml) for 2 h. The mixture was then partitioned between diethyl ether and aqueous 1N HCL, the layers were separated, the organic layer was dried over sodium sulphate, and evaporated off to give the desired 1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid [4-((R)-3-hydroxy-1-trifluoromethyl-propoxy)-phenyl]-amide (0.073 g) as light brown crystalline solid. MS (ESI): 501.2 (MH+).

Workup

  1. customThe mixture was then partitioned between diethyl ether and aqueous 1N HCL
  2. customthe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulphate
  4. customevaporated off

Sources & evidence

ORD record
ord-6511b44a98774b77a45711610c98b2bd
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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