Hexahydro-1,4-diazepine → 5,5'-[1,4-diazepane-1,4-diylbis(1-hydroxyethane-2,1-diyl)]bis(4-methyl-2-benzofuran-1(3H)-one)

HRID 1474360Notes

Reaction equation

HRID 1474360 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C@H:12]1[CH2:14][O:13]1.[CH3:15][C:16]1[C:24]2[CH2:23][O:22][C:21](=[O:25])[C:20]=2[CH:19]=[CH:18][C:17]=1[CH:26]1[CH2:28][O:27]1.[NH:29]1[CH2:35][CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[N:29]1([CH2:28][CH:26]([C:17]2[CH:18]=[CH:19][C:20]3[C:21](=[O:25])[O:22][CH2:23][C:24]=3[C:16]=2[CH3:15])[OH:27])[CH2:35][CH2:34][CH2:33][N:32]([CH2:14][CH:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[CH3:1])[OH:13])[CH2:31][CH2:30]1

Participants

4

Reactant 3

HCID 68163Hexahydro-1,4-diazepineHCID 552705554-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-oneHCID 59568665(S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one

Product 1

HCID 498041845,5'-[1,4-diazepane-1,4-diylbis(1-hydroxyethane-2,1-diyl)]bis(4-methyl-2-benzofuran-1(3H)-one)

Procedure

The reaction was run in a similar fashion to general epoxide opening conditions as shown for EXAMPLE 2 (at 150° C. for 60 min) starting from 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one and 1,4-diazepane. Purification by preparative TLC (MeOH/DCM=1:15) afforded 5,5′-[1,4-diazepane-1,4-diylbis(1-hydroxyethane-2,1-diyl)]bis(4-methyl-2-benzofuran-1(3H)-one) The resulting mixture of isomers was then separated to all three pure diastereomers by SFC chiral chromatography.

Workup

  1. customas shown for EXAMPLE 2 (at 150° C. for 60 min)
  2. customPurification by preparative TLC (MeOH/DCM=1:15)

Sources & evidence

ORD record
ord-8adbc17c538742b5a91d015b406a3b47
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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