((1S,2S)-2-(4-bromophenyl)cyclopropyl)methanol → 2-[(1s,2r)-2-(4-Bromophenyl)cycloprop-1-yl]ethanol

HRID 73304Notes

Reaction equation

HRID 73304 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@@H:9]2[CH:11]=[CH2:12])=[CH:4][CH:3]=1.BrC1C=CC([C@H]2C[C@@H]2C[OH:24])=CC=1>CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][CH2:12][OH:24])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 57515373((1S,2S)-2-(4-bromophenyl)cyclopropyl)methanolHCID 684062521-Bromo-4-[(1S,2R)-2-vinylcyclopropyl]benzene

Product 1

HCID 684076812-[(1s,2r)-2-(4-Bromophenyl)cycloprop-1-yl]ethanol

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The alkene intermediate from Example 29F (1.64 g, 7.35 mmol) was converted to the alcohol by the method of Example 26F, followed by chromatography (7.3 hexane/ethyl acetate) provided the title compound. 1H NMR (300 MHz, CDCl3): δ 0.96-0.79 (m, 2H), 1.00-1.14 (m, 1H), 1.54-1.76 (m, 3H), 4.91-4.97 (m, 1H), 3.76 (t, J=6 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 7.35 (d, J=9 Hz, 2H). MS (DCl—NH3) m/z 258 (M+NH4)+.

Sources & evidence

ORD record
ord-e53350ad33154e8597d16f746643e1ce
Source dataset
uspto-grants-2014_09
Patent number
US08829041B2

Reaction notes

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