2-Cyclohexen-1-one → HCID 39240598, compound

HRID 1803773Notes

Reaction equation

HRID 1803773 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=C1.[CH3:8][N:9]([CH3:19])[C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(C1C=CC(B(O)O)=CC=1)(C)(C)C>>[CH3:8][N:9]([CH3:19])[C:10]1[CH:15]=[CH:14][C:13]([C@H:5]2[CH2:4][CH2:3][C:1](=[O:7])[CH2:6]2)=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 135942-Cyclohexen-1-oneHCID 27343204-tert-Butylphenylboronic acidHCID 27343444-(Dimethylamino)phenylboronic acid

Product 1

HCID 39240598HCID 39240598, compound

Procedure

The title compound was prepared using the procedure as described in Example 28A, substituting 2-cyclopenten-1-one for cyclohexen-1-one, S-BINAP and 4-(dimethylamino)-phenylboronic acid for 4-(tertbutyl)-phenylboronic acid. The mixture was purified on SiO2 (hexane/ethyl acetate 4/1) to provide the title compound. [α]D=−22.31 c=1.0 (CH3OH). 1H NMR (CD3OD, 300 MHz); δ 1.85-2.01 (m, 1H), 2.21-2.40 (m, 4H), 2.42-2.50 (m, 1H), 2.88 (s, 6H), 3.29-3.39 (m, 1H), 6.78-6.81 (m, 2H), 7.11-7.21 (m, 2H). MS (DCI) m/z 204 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThe mixture was purified on SiO2 (hexane/ethyl acetate 4/1)

Sources & evidence

ORD record
ord-83f465ed38224af2a2aaedb789c64411
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

Loading…