Hydrochloric Acid → HCID 22406803, compound

HRID 440497Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH:16]2[C:19]2([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)[CH2:22][CH2:21][CH2:20]2)=[CH:11][C:10]=1[O:34][CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:38]([BH3-])#N.[Na+].[OH-].[Na+].Cl>CCOCC.C(O)(=O)C.C(#N)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]([CH3:38])[CH:16]2[C:19]2([C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]([F:33])([F:31])[F:32])=[CH:27][CH:28]=3)[CH2:20][CH2:21][CH2:22]2)=[CH:11][C:10]=1[O:34][CH3:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of 7-benzyloxy-6-methoxy-1-[1-(4-trifluoromethoxyphenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline (4.1 g, prepared in a similar manner to that described in Example RC18), 37-40% aqueous formaldehyde solution (4.4 ml), acetonitrile (90 ml) and sodium cyanoborohydride (2.32 g) was stirred at 5° C. for 15 minutes, then neutralised with glacial acetic acid and stirred for a further 16 hours. The mixture was poured into dilute aqueous sodium hydroxide solution and extracted with ethyl acetate. The extracts yielded a gum which was dissolved in ether and treated with hydrogen chloride to give 7-benzyloxy-6-methoxy-2-methyl-1-[1-(4-trifluoromethoxyphenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline as the hydrochloride salt.

Workup

customprepared in a similar manner to that
stirringstirred for a further 16 hours
extractionextracted with ethyl acetate
customThe extracts yielded a gum which

Sources & evidence

ORD record: ord-952071a9b4d742a69d2a84f75c566040
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05519034

Reaction notes

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