tert-Butyldimethylsilyl chloride → Methyl 6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 658800Notes

Reaction equation

HRID 658800 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6]2.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18]>>[Si:21]([O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6]2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 66974808Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

Product 1

HCID 59524387Methyl 6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydroisoquinoline-3-carboxylateYield 83%

Procedure

Prepared as in Example 12-1c from methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride (Example 13-3c) and tert-butylchlorodimethylsilane. Yield 83%, yellowish. MS 322 (MH+).

Sources & evidence

ORD record
ord-26028ea3991c4b33a5ef4646b9d2b151
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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