(S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline → (S)-tert-Butyl 3-(3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-iodobenzoate

HRID 528983Notes

Reaction equation

HRID 528983 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([I:17])=[C:12]([CH:16]=1)[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si:18]([O:25][CH2:26][C@@H:27]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][NH:28]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>>[Si:18]([O:25][CH2:26][C@@H:27]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][N:28]1[C:13]([C:12]1[CH:16]=[C:8]([CH:9]=[CH:10][C:11]=1[I:17])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 10333747(S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinolineHCID 71061145HCID 71061145, compound

Product 1

HCID 71062376(S)-tert-Butyl 3-(3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-iodobenzoateYield 54%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223A, 5-(tert-butoxycarbonyl)-2-iodobenzoic acid (1.67 g, 4.81 mmol) and (S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline (1.6 g, 5.8 mmol) were converted to the title compound (1.57 g, 54%). MS(ESI+) m/z 608.1 (M+H)+.

Sources & evidence

ORD record
ord-10346d209649418891d96182cd046462
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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