Sodium borohydride → N'-[2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]-N,N-diethylsulfuric diamide hydrochloride

HRID 242071Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26](=[O:33])(=[O:32])[N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:20]=4)[C:15]([CH3:35])([CH3:34])[CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26](=[O:32])(=[O:33])[N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:20]=4)[C:15]([CH3:35])([CH3:34])[CH2:14][NH:13]3)[CH2:9][CH2:10][CH2:11]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 66868671N'-[2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]-N,N-diethylsulfuric diamide

Product 1

HCID 66868967N'-[2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]-N,N-diethylsulfuric diamide hydrochloride

Procedure

N′-[2-({1-[1-(4-Chlorophenyl)cyclobutyl]-4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]-N,N-diethylsulfuric diamide hydrochloride was prepared analogously to example 65 using N′-[2-({1-[1-(4-chlorophenyl)cyclobutyl]-4,4-dimethyl-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]-N,N-diethylsulfuric diamide (68 mg, 0.13 mmol) and sodiumborohydride (10 mg, 0.26 mmol). Yield: 60 mg (0.11 mmol, 82%, colorless foam).

Sources & evidence

ORD record: ord-8a2673588e1143ad951fe9fd984d349f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653100B2

Reaction notes

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