Boron tribromide → {1-[(4-Phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methanol

HRID 1180768Notes

Reaction equation

HRID 1180768 reaction equation
C([O:8][CH2:9][C:10]1([CH2:14][C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH2:13][CH2:12][CH2:11]1)C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[C:20]1([C:18]2[N:19]=[C:15]([CH2:14][C:10]3([CH2:9][OH:8])[CH2:13][CH2:12][CH2:11]3)[S:16][CH:17]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 112102692-({1-[(Benzyloxy)methyl]cyclobutyl}methyl)-4-phenyl-1,3-thiazole

Product 1

HCID 11737047{1-[(4-Phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methanolYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.7 g (2.0 mmol) of 2-({1-[(benzyloxy)methyl]cyclobutyl}methyl)-4-phenyl-1,3-thiazole in 15 mL of dichloromethane was added a 1.0 M solution of 2.2 mL (2.2 mmol) of boron tribromide and the contents stirred at room temperature for 16 h. After quenching with 10 mL of methanol, the contents were concentrated under vacuum and the residue was purified by silica gel chromatography using ethyl acetate:hexane (1:9) as the eluent to afford 0.16 g (31%) of {1-[(4-phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 4.13 (t, J=7 Hz, 1H), 3.66 (d, J=6 Hz, 2H), 3.3 (s, 2H), 2.08-1.94 (m, 6H). GC-MS m/z 260 (M+H).

Workup

  1. customAfter quenching with 10 mL of methanol
  2. concentrationthe contents were concentrated under vacuum
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b719fed585324370beb4d16dd26749cb
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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