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Methanol → (R)-2-Methyl-1-oxo-1-(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-yl acetate

HRID 445279
Notes
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Reaction equation

HRID 445279 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:30]([O:33][C:34]([C:37](Cl)=[O:38])([CH3:36])[CH3:35])(=[O:32])[CH3:31].CO>C(Cl)Cl>[C:30]([O:33][C:34]([CH3:36])([CH3:35])[C:37](=[O:38])[N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=1)(=[O:32])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 1234962-Acetoxyisobutyroyl chloride2×HCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536313(R)-2-Methyl-1-oxo-1-(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-yl acetate

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (207 mg, 747 μmol, example 30 (step 1) and DIEA (130 μL, 747 μmol) in DCM (2.5 mL) was added 1-chlorocarbonyl-1-methylethyl acetate (119 μL, 821 μmol). The mixture was stirred at RT for 3 h. Then, 1-chlorocarbonyl-1-methylethyl acetate (50 μL) was added and the mixture was stirred at RT for 16 h. MeOH (1 mL) was added and the mixture was filtered. The filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/water 0.1% TFA) to give the title compound in a solution of H2O 0.1% TFA and MeCN 0.1% TFA. The solvent was removed and saturated NaHCO3 (5 mL) was added. The mixture was extracted with EtOAc (2×30 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to give the title compound as a white solid. MS (ESI, positive ion) m/z: 406 (M+H).

Workup

  1. stirringthe mixture was stirred at RT for 16 h
  2. filtrationthe mixture was filtered
  3. customThe filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/water 0.1% TFA)

Sources & evidence

ORD record
ord-1788a70662394664921c8942a9e49528
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08476297B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes