HCID 10492437, compound → HCID 11266577, compound

HRID 1045240Notes

Reaction equation

O[C@H](CCCCCCCCCC(C)C)CC(OC)=O.[CH3:20][CH:21]([CH3:40])[CH2:22][CH:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33](=[O:39])[CH2:34][C:35]([O:37][CH3:38])=[O:36]>>[OH:39][C@H:33]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH:21]([CH3:40])[CH3:20])[CH2:34][C:35]([O:37][CH3:38])=[O:36]

Participants

Reactant 2

HCID 10492437HCID 10492437, compound

HCID 86644994HCID 86644994, compound

Product 1

HCID 11266577HCID 11266577, compoundYield 92%

Procedure

In a manner similar to the synthesis of compound 114, compound 113 (100 mg, 0.338 mmol) was reduced by a two step procedure to afford 115 as a colorless oil (93 mg, 92%, two steps). Rf=0.50 (hexane/ethyl acetate, 4/1, v/v); [α]25D=−6.0° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ 3.95 (m, 1H, H-3), 3.66 (s, 3H, OCH3), 2.47 (dd, 1H, J2a,2b=16.2 Hz, J2a,3=3.3 Hz, H-2a), 2.36 (dd, 1H, J2a,2b=16.2 Hz, J2b,3=9.0 Hz, H-2b), 1.53-1.32 (m, 3H, H-4, H-15), 1.21-1.03 [m, 20H, H-(5-14)], 0.81 (d, 6H, J15,16=6.3 Hz, H-16); 13C NMR (75 MHz, CDCl3): δ 173.47 (C═O), 67.97 (C-3), 51.67 (CH3O), 41.08 (C-2), 39.02 (C-12), 36.51 (C-4), 22.62 (C-14). HR MS (m/z) calculated for C18H36O3 [M+Na], 323.2557; found, 323.1925.

Sources & evidence

ORD record: ord-00093f3c49df4ae5893a9430bb1a6e11
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563523B2

Reaction notes

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