Hydrochloric Acid → 5-Ethyl-2-methyl-4-propyl-4,5,5a,6-tetrahydrodibenzo[cd,f]indole-9,10-diol

HRID 746009Notes

Reaction equation

HRID 746009 reaction equation
[CH2:1]([N:3]1[C@H:11]2[C:6]3=[C:7]([CH:20]=[C:21]([CH3:23])[CH:22]=[C:5]3[C@@H:4]1[CH2:24][CH2:25][CH3:26])[C:8]1[C:15]([O:16]C)=[C:14]([O:18]C)[CH:13]=[CH:12][C:9]=1[CH2:10]2)[CH3:2].Cl>CO>[CH2:1]([N:3]1[C@H:11]2[C:6]3=[C:7]([CH:20]=[C:21]([CH3:23])[CH:22]=[C:5]3[C@@H:4]1[CH2:24][CH2:25][CH3:26])[C:8]1[C:15]([OH:16])=[C:14]([OH:18])[CH:13]=[CH:12][C:9]=1[CH2:10]2)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13772989HCID 13772989, compound

Product 1

HCID 1459355-Ethyl-2-methyl-4-propyl-4,5,5a,6-tetrahydrodibenzo[cd,f]indole-9,10-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Proceeding as described in Example 1(g), (-)-(4S,5aR)-5-ethyl-4,5,5a,6-tetrahydro-9,10-dihydroxy-2-methyl-4-n-propyl-dibenz[cd,f]indole hydrobromide is obtained from the tartrate obtained above under (a). The corresponding hydrochloride melts at above 160° with decomposition; [α]D20 =-94° (c=0.5 in methanol).

Sources & evidence

ORD record
ord-75a6efa493c94c399f2bb3cb0f597cdc
Source dataset
uspto-grants-1986_07
Patent number
US04602032

Reaction notes

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