Hydrochloric Acid → (1S,3R)-5-Bromo-3-[[(tert-butyldimethylsilyl)oxy]methyl]-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 1854559Notes

Reaction equation

HRID 1854559 reaction equation
[ClH:1].[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][C@H:6]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[NH:7][C@H:8]2[CH3:13]>C(OC(C)C)(=O)C>[ClH:1].[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][C@H:6]([CH2:14][O:15][Si:16]([C:19]([CH3:20])([CH3:22])[CH3:21])([CH3:18])[CH3:17])[NH:7][C@H:8]2[CH3:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118998349(1S,3R)-5-Bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 122412747(1S,3R)-5-Bromo-3-[[(tert-butyldimethylsilyl)oxy]methyl]-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 87.3%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

Add hydrogen chloride (267.24 g, 1.02 mol, 4M in 1,4-dioxane) to (1S,3R)-5-bromo-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline (419 g, 1.02 mol) in isopropyl acetate (4.19 L) at 10° C. and stir for 15 minutes in an appropriate vessel. Filter the mixture and wash the filter cake with isopropyl acetate (2.5 L), dry on the filter for 30 minutes, then under vacuum in an oven at 40° C. for 16 hours to give the title compound (380 g, 0.89 mol). MS (m/z): 370(M-Cl (79Br)), 372(M-Cl (81Br)).

Workup

  1. filtrationFilter the mixture
  2. washwash the filter cake with isopropyl acetate (2.5 L)
  3. customdry on the
  4. filtrationfilter for 30 minutes

Sources & evidence

ORD record
ord-9df5d0b155dd479e81be6b737614cff5
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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