Benzyl Bromide → (1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-ol

HRID 46102

Reaction equation

[C@@H:1]12[CH2:8][C@@H:4]([C@@H:5]([OH:7])[CH2:6]1)[CH2:3][C@@H:2]2[OH:9].C1OCCOCCOCCOCCOC1.O1CCCC1.[OH-].[Na+].Br[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([O:7][C@H:5]1[CH2:6][C@H:1]2[CH2:8][C@@H:4]1[CH2:3][C@@H:2]2[OH:9])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Reactant 5

HCID 7498Benzyl Bromide

HCID 8028Tetrahydrofuran

HCID 14798Sodium Hydroxide

HCID 3633615-Crown-5

HCID 9989289(1R,2S,4R,5S)-Bicyclo[2.2.1]heptane-2,5-diol

Product 1

HCID 10036335(1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-ol

Conditions

Temperature: 10 °C

Procedure

To a stirred solution of (1R,2S,4R,5S)-bicyclo[2.2.1]-heptane-2,5-diol (1.15 g, 8.97 mmol) and 15-crown-5 (0.054 mL, 0.269 mmol) in tetrahydrofuran (30.0 mL, 8.97 mmol) were added at 10° C. (ice/water bath) finely ground sodium hydroxide (2.15 g, 53.8 mmol) and 1-(bromomethyl)benzene (1.07 mL, 8.97 mmol). After stirring at 10° C. for 3 h, the mixture was stirred at ambient temperature overnight. The mixture was partitioned between EtOAc and water, and the organic portions were washed with brine, and conc. in vacuo. The crude product was purified by flash column chromatography (0 to 80% of ethyl acetate in hexanes). The title compound was obtained as a colorless oil.

Workup

stirringthe mixture was stirred at ambient temperature overnight
customThe mixture was partitioned between EtOAc and water
washthe organic portions were washed with brine
customThe crude product was purified by flash column chromatography (0 to 80% of ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-0398e47c3d9a4f728465e8b40c186dab
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541592B2

Linked notes

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