Cesium fluoride → HCID 68501142, compound

HRID 1176493Notes

Reaction equation

HRID 1176493 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH:9]2[O:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]3[O:34][CH2:33][C:32](=[O:35])[N:31]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:30]=3[CH:41]=2)=[CH:4][CH:3]=1.[O:42]([CH2:49][C@@H:50]1[CH2:52][O:51]1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[F-].[Cs+]>>[OH:51][C@H:50]([CH2:49][O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:52][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:10][CH:9]2[O:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]3[O:34][CH2:33][C:32](=[O:35])[N:31]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:30]=3[CH:41]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 25953Cesium fluorideHCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 68500605HCID 68500605, compound

Product 1

HCID 68501142HCID 68501142, compound

Conditions

Temperature
130 °C

Procedure

The mixture of 0.280 g of benzyl 4-(4-hydroxyphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate, 0.152 g of 2(S)-phenoxymethyloxirane and 0.0015 g of caesium fluoride is stirred at 130° C. over 3 hours. The reaction mixture is cooled and the title compound is obtained as a colourless oil by means of flash chromatography (SiO2 60F). Rf=0.13 (1:1 EtOAc-heptane); Rt=5.14.

Workup

  1. temperatureThe reaction mixture is cooled

Sources & evidence

ORD record
ord-0281f0d5b4814ea8aa2bf5da87948e65
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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