cis-2,6-dimethyloxan-4-one → rel-(2R,6S)-4-[2,3-Dihydro-2-(phenylmethyl)-1H-isoindol-5-yl]tetrahydro-2,6-dimethyl-2H-pyran-4-ol

HRID 225649Notes

Reaction equation

HRID 225649 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][C@@H:19]1[CH2:24][C:23](=[O:25])[CH2:22][C@H:21]([CH3:26])[O:20]1>>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:23]3([OH:25])[CH2:22][C@@H:21]([CH3:26])[O:20][C@@H:19]([CH3:18])[CH2:24]3)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 10441716cis-2,6-dimethyloxan-4-oneHCID 534165502-Benzyl-5-bromoisoindoline

Product 1

HCID 57753466rel-(2R,6S)-4-[2,3-Dihydro-2-(phenylmethyl)-1H-isoindol-5-yl]tetrahydro-2,6-dimethyl-2H-pyran-4-ol

Procedure

Prepared in analogy to Example A62(b) from 2-benzyl-5-bromo-2,3-dihydro-1H-isoindole (Example A62(a)) and (2R,6S)-2,6-dimethyl-tetrahydro-pyran-4-one. Brown solid. MS (m/e): 338.4 ([M+H]+, 100%).

Sources & evidence

ORD record
ord-31903a586e1a428ab283b05e17606acc
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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