Pentane → HCID 22676882, compound

HRID 991967Notes

Reaction equation

HRID 991967 reaction equation
[CH2:1]([O:8][CH:9]([CH3:18])[CH2:10][CH2:11][C:12]1[C:13](=[O:17])[CH2:14][CH2:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCC>C(OCC)C>[CH2:1]([O:8][CH:9]([CH3:18])[CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8003PentaneHCID 22676876HCID 22676876, compound

Product 1

HCID 22676882HCID 22676882, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

General procedure B using (S)-p-tol-BfNAP and 3-benzyloxybutyl-cyclopent-2-enone (0.146 g, 0.6 mmol) gave, after 30 h at 0° C. and flash chromatography (1:2 pentane:diethyl ether), the title compound as a clear oil (0.139 g, 94% yield). 1H NMR (300 MHz, CDCl3): δ7.37-7.23 (m, 5 H), 4.50 (s, 2 H), 3.47 (t, J=6.3 Hz, 2 H), 2.43-2.04 (m, 5 H), 1.78 (ddd, J=18.0, 9.6, 1.2 Hz, 1 H), 1.70-1.56 (m, 2 H), 1.56-1.34 (m, 5 H). 13C NMR (75 MHz, CDCl3): δ219.8, 138.6, 128.4, 127.7, 127.6, 73.1, 70.3, 45.4, 38.7, 37.4, 35.7, 30.0, 29.7, 24.8. IR (neat): 2934, 2860, 1741, 1455, 1405, 1363, 1158, 1100, 737, 699 cm−1. HRMS m/z calcd for C16H22O2 246.1620, obsd 246.1615. [α]D25° C.−89° (c 1.4, CHCl3). Chiral HPLC analysis (Chiracel OD column) indicated that the title compound was obtained in 94% ee.

Workup

  1. customgave, after 30 h at 0° C.

Sources & evidence

ORD record
ord-082e2e706c23443aa7a54032770023a9
Source dataset
uspto-grants-2002_10
Patent number
US06465664B1

Reaction notes

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