5,11-Dihydrodibenzo[b,e][1,4]oxazepine → (+)-5,11-dihydro-5-[[(2R, 4R)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine

HRID 365333Notes

Reaction equation

HRID 365333 reaction equation
Cl[C@H:2]1[CH2:7][C@@H:6]([O:8][CH2:9][O:10][CH3:11])[CH2:5][N:4]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:3]1.[CH:22]1[C:32]2[CH2:31][O:30][C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[NH:27][C:26]=2[CH:25]=[CH:24][CH:23]=1>>[CH3:11][O:10][CH2:9][O:8][C@H:6]1[CH2:5][N:4]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C@@H:2]([CH2:3][N:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:32]=3[CH2:31][O:30][C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]2=3)[CH2:7]1

Participants

3

Reactant 2

HCID 110847985,11-Dihydrodibenzo[b,e][1,4]oxazepineHCID 15481952(3S,5R)-(+)-3-chloro-5-(methoxymethoxy)-1-(4-methoxyphenethyl)piperidine

Product 1

HCID 15481938(+)-5,11-dihydro-5-[[(2R, 4R)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine

Procedure

(3S,5R)-(+)-3-chloro-5-(methoxymethoxy)-1-(4-methoxyphenethyl)piperidine was coupled with 5,11-dihydrodibenzo[b,e][1,4]oxazepine as described in Example 1 to give (+)-5,11-dihydro-5-[[(2R,4R)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine in 4.30 g (72.6%) yield as pale yellow oil.

Sources & evidence

ORD record
ord-153fd8efd25f4a52bba6db54503188c8
Source dataset
uspto-grants-2000_10
Patent number
US06127361

Reaction notes

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