Boron tribromide → HCID 51001491, compound

HRID 2381184Notes

Reaction equation

HRID 2381184 reaction equation
[F:1][C:2]([F:34])([F:33])[CH:3]([CH2:30][O:31]C)[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:14]2[CH2:19][CH2:18][N:17]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:16][CH2:15]2)=[O:13])=[CH:7][CH:6]=1.B(Br)(Br)Br>C(Cl)Cl.C(OCC)C>[F:34][C:2]([F:1])([F:33])[CH:3]([CH2:30][OH:31])[O:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([CH:14]2[CH2:15][CH2:16][N:17]([S:20]([C:23]3[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=3)(=[O:22])=[O:21])[CH2:18][CH2:19]2)=[O:13])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 51001570HCID 51001570, compound

Product 1

HCID 51001491HCID 51001491, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (rac)-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid [4-(2,2,2-trifluoro-1-methoxymethyl-ethoxy)-phenyl]-amide (240 mg), product of example 54) in methylene chloride was treated at RT and under an argon atmosphere with BBr3 (0.5 molar in methylene chloride, 2 ml) and stirred 2 h at RT. The reaction mixture was then taken up in diethyl ether, washed with aqueous 1N HCl, the layers were separated, the organic layer dried over sodium sulfate and evaporated off to give the desired (rac)-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid [4-(2,2,2-trifluoro-1-hydroxymethyl-ethoxy)-phenyl]-amide crystalline light red solid. MS (ESI): 487.3 (MH+).

Workup

  1. washwashed with aqueous 1N HCl
  2. customthe layers were separated
  3. dry with materialthe organic layer dried over sodium sulfate
  4. customevaporated off

Sources & evidence

ORD record
ord-c0ffd4ad9bfa417eafed2d074f363432
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

Loading…