2-Methyl-3-butyn-2-ol → HCID 54166101, compound

HRID 1607023Notes

Reaction equation

HRID 1607023 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[N:8]3[CH2:17][CH2:18][CH2:19][C@H:7]3[C:6]=12.[CH3:20][C:21]([OH:25])([C:23]#[CH:24])[CH3:22]>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[OH:25][C:21]([CH3:22])([CH3:20])[C:23]#[C:24][C:2]1[N:3]=[CH:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[N:8]3[CH2:17][CH2:18][CH2:19][C@H:7]3[C:6]=12

Participants

6

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 54331352HCID 54331352, compound

Product 1

HCID 54166101HCID 54166101, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

3.65 g (10 mmol) of (S)-11,12,13,13a-tetrahydro-1-iodo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one was heated to boiling under reflux for 1.5 hours with 1.26 g (15 mmol) of 2-methyl-3-butyn-2-ol, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 20 mg of copper(I) iodide in 30 ml of diethylamine. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. By recrystallization of the crude product from methanol and water there was obtained (S)-11,12,13,13a-tetrahydro-1-(3-hydroxy-3-methyl-1-butynyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 128°.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on silica gel
  3. washwhile eluting with ethyl acetate
  4. customBy recrystallization of the crude product from methanol

Sources & evidence

ORD record
ord-5fe2a79e19334734b1602da279091465
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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