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Methyl iodide → 10-{4-[(3R)-3-Methoxy-2-methylcyclohex-1-en-1-yl]-3-methylbenzoyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 1794023
Notes
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Reaction equation

HRID 1794023 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH2:28][CH2:27][CH2:26][C@@H:25]([OH:29])[C:24]=4[CH3:30])=[C:19]([CH3:31])[CH:18]=3)=[O:16])[CH2:6][C:5]=12.[H-].[Na+].[H][H].[CH3:36]I>O1CCCC1>[CH3:36][O:29][C@@H:25]1[CH2:26][CH2:27][CH2:28][C:23]([C:20]2[CH:21]=[CH:22][C:17]([C:15]([N:7]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[CH2:10][N:4]4[CH:3]=[CH:2][CH:1]=[C:5]4[CH2:6]3)=[O:16])=[CH:18][C:19]=2[CH3:31])=[C:24]1[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 69313729(10, 11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-((3R)-3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 6965259710-{4-[(3R)-3-Methoxy-2-methylcyclohex-1-en-1-yl]-3-methylbenzoyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine
Yield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-((3R)-3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone of Example 41 (0.125 g, 0.303 mmol) was dissolved in anhydrous tetrahydrofuran (3.0 mL) followed by addition of sodium hydride (0.008 g, 0.333 mmol). After hydrogen gas evolution ceased (5 minutes), methyl iodide (0.038 mL, 0.606 mmol) was added and the reaction stirred for 30 minutes. Additional sodium hydride (0.008 g, 0.333 mmol) was added and stirring continued overnight. The reaction was quenched with saturated ammonium chloride (50 mL) and extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. Purification of the residue by flash column chromatography, eluting with 30% ethyl acetate in hexane, followed by recrystallization from petroleum ether afforded the title compound (0.120 g) as white crystals, m.p. 127–128° C.; [α]D=+45.65 (c=1.0, chloroform). Single crystal X-ray crystallography established the absolute configuration as the (R)-isomer.

Workup

  1. additionwas added
  2. stirringstirring continued overnight
  3. customThe reaction was quenched with saturated ammonium chloride (50 mL)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by flash column chromatography
  9. washeluting with 30% ethyl acetate in hexane
  10. customfollowed by recrystallization from petroleum ether

Sources & evidence

ORD record
ord-ee7db355ab6d4314a6a982eb170a2214
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07022699B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes