Ethanol → (10,11-Dihydro-5h-pyrrolo-[2,1-c][1,4]benzodiazepin-10-yl)-[4-((3s)-3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone

HRID 1794022Notes

Reaction equation

HRID 1794022 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH2:28][CH2:27][CH2:26][CH:25]([OH:29])[C:24]=4[CH3:30])=[C:19]([CH3:31])[CH:18]=3)=[O:16])[CH2:6][C:5]=12.C(O)C>CCCCCC>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH2:28][CH2:27][CH2:26][C@H:25]([OH:29])[C:24]=4[CH3:30])=[C:19]([CH3:31])[CH:18]=3)=[O:16])[CH2:6][C:5]=12

Participants

4

Reactant 2

HCID 702EthanolHCID 10273123Racemic (10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-[4-(3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone

Product 1

HCID 21021806(10,11-Dihydro-5h-pyrrolo-[2,1-c][1,4]benzodiazepin-10-yl)-[4-((3s)-3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Racemic (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone of Example 5 was subjected to chiral HPLC (Chiralpak AD, 21.1×250 mm, 50% ethanol in hexane). The second peak which eluted displayed a negative optical rotation and was arbitrarily assigned the (S)-configuration. The title compound was isolated as a white solid, [α]D=−36.69 (c=1.0, chloroform).

Workup

  1. washThe second peak which eluted

Sources & evidence

ORD record
ord-f3cb23d60d7f422c8b4a21a6bdb31ec4
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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