HCID 11522987, compound → HCID 86591983, compound

HRID 1351751Notes

Reaction equation

[C:1]([C:3]1[CH:11]=[C:10]([CH2:12][OH:13])[C:9]([CH3:14])=[C:8]2[C:4]=1[C:5]1[CH2:18][CH2:17][O:16][C:15]([CH2:22][C:23]([OH:25])=[O:24])([CH2:19][CH2:20][CH3:21])[C:6]=1[NH:7]2)#[N:2].Cl[CH:27](Cl)[CH3:28].C1C=CC=CC=1>CCOC(C)=O.O=[Mn]=O>[CH2:27]([O:24][C:23](=[O:25])[CH2:22][C:15]1([CH2:19][CH2:20][CH3:21])[C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH2:18][CH2:17][O:16]1)=[C:3]([C:1]#[N:2])[CH:11]=[C:10]([CH:12]=[O:13])[C:9]=3[CH3:14])[CH3:28]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (5-cyano-7-hydroxymethyl-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid (8.28 g, 22 mmol) in dichloroethane/benzene (85 mL/85 mL) was added a homogeneous mixture of activated MnO2 (19.4 g, 223 mmol) and Celite (19.4 g). The solution was heated to 40° C. and agitated vigorously for 1.3 hours. The reaction was cooled, diluted with EtOAc and filtered through Celite. Concentration of the filtrate in vacuo afforded 7.88 g (96%) of a pale yellow foam. 1H NMR (CDCl3) δ 10.31 (bs, 1 H), 10.27 (s, 1H), 7.90 (s, 1H), 4.27 (m, 2H), 4.11 (m, 1H), 3.95 (m, 1H), 3.09 (m, 2H), 3.04 (d, J=17.0 Hz, 1H), 2.95 (d, J=7.6 Hz, 1H), 2.57 (s, 3H), 2.00 (m, 2H), 1.30 (m, 4H), 0.90 (t, J=7.62 Hz, 2H).

Workup

temperatureThe reaction was cooled
filtrationfiltered through Celite

Sources & evidence

ORD record: ord-370f3e394bda4d0481ef00623eacff91
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217730B2

Reaction notes

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