3-Chloro-1-propanol → (R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 566957Notes

Reaction equation

[Cl-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C@H:10]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18](OC)[CH:17]=1)[N+:9]([CH2:32]C)(CCCO)[CH2:8][CH2:7]2.[CH2:34](I)C.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.ClCCCO>>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C@@H:10]([CH2:16][C:17]1[CH:34]=[CH:21][C:20]([O:22][CH3:23])=[C:19]([O:24][CH3:25])[CH:18]=1)[N:9]([CH3:32])[CH2:8][CH2:7]2

Participants

Reactant 3

HCID 123133-Chloro-1-propanol

HCID 20639462HCID 20639462, compound

HCID 86756254HCID 86756254, compound

Product 1

HCID 978314(R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Procedure

(1S,2RS)-6,7-Dimethoxy-2-ethyl-2-(3-hydroxypropyl)-1-(3,4,5-trimethoxyphenyl )-1,2,3,4-tetrahydroisoquinolinium chloride [(1S,2R)/(1S,2S), 2:1] was prepared by alkylation with ethyl iodide/potassium carbonate/dimethylformamide followed by quaternization with 3-chloropropanol (see Synthetic Example 1, procedure a).

Sources & evidence

ORD record: ord-429a7a3c876549aa908bc4ceb686bebe
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177445B1

Reaction notes

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