Diisopropylethylamine → HCID 20448827, compound

HRID 358377Notes

Reaction equation

HRID 358377 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][C:11](=[O:13])[CH:10]([CH2:14]OS(C)(=O)=O)[CH:9]1/[CH:20]=[CH:21]/[CH:22]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].OCC1CCCC1=O.C(N(C(C)C)CC)(C)C>CCOCC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][C:11](=[O:13])[C:10](=[CH2:14])[CH:9]1/[CH:20]=[CH:21]/[CH:22]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 110945752-(Hydroxymethyl)cyclopentanoneHCID 86739604HCID 86739604, compound

Product 1

HCID 20448827HCID 20448827, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a similar way to Example 24, (1), 293 mg of crude 4(RS)-(tetrahydropyran-2-yloxy)-3(RS)-[3-(tetrahydropyran-2-yloxy)-trans-1-octenyl]-2(SR)-(methanesulfonyloxymethyl)cyclopentanone was prepared from 243 mg of 4(RS)-(tetrahydropyran-2-yloxy)-3(RS)-]3-(tetrahydropyran-2-yloxy)trans-1-octenyl]-2(SR)-(hydroxymethyl)cyclopentanone. The crude product was reacted with diisopropylethylamine in ether in a similar way to Example 24, (2) to give 239 mg of crude 4(RS)-(tetrahydropyran-2-yloxy)-3(RS)-[3-(tetrahydropyran-2-yloxy)trans-1-octenyl]-2-methylidenecyclopentanone.

Sources & evidence

ORD record
ord-ffd5c50e9e464a638b1e917c75a9e8a1
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

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