(R)-3-(4-Bromophenyl)cyclopentan-1-one → Ethyl [(3R)-3-(4-bromophenyl)cyclopentylidene]acetate

HRID 1713849Notes

Reaction equation

HRID 1713849 reaction equation
C(O[C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19]C[C:17](=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.NC1C=CC(C2CCCC(CC(OCC)=O)C2)=CC=1.[Br:46]C1C=CC([C@@H]2CCC(=O)C2)=CC=1>>[Br:46][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]2[CH2:20][CH2:19][C:17](=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:16]2)=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 49833221(R)-3-(4-Bromophenyl)cyclopentan-1-oneHCID 59464273Ethyl 2-(3-(4-aminophenyl)cyclohexyl)acetateHCID 72292906Ethyl {3-[4-(benzyloxy)phenyl]cyclohexylidene}acetate

Product 1

HCID 86619813Ethyl [(3R)-3-(4-bromophenyl)cyclopentylidene]acetate

Procedure

Following the general procedure described for ethyl {3-[4-(benzyloxy)phenyl]cyclohexylidene}acetate (Intermediate 89 (ii)), replacing 3-[4-(benzyloxy)phenyl]cyclohexanone with (3R)-3-(4-bromophenyl)cyclopentanone the title compound was obtained; 1H NMR δ1.18-1.23 (3H, m), 1.61-1.78 (1H, m), 2.06-2.20 (1H, m), 2.53-2.67 (3H, m), 2.84-3.04 (1H, m), 3.08-3.24 (1H, m), 4.01-4.10 (2H, m), 5.82-5.85 (1H, m), 7.24-7.28 (2H, m), 7.47-7.51 (2H, m); MS m/e MH+ 310.

Sources & evidence

ORD record
ord-722e3fd2466149c58e30f557c9387e33
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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