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Triphenylphosphine → (7S,8aS)-7-(3-Cyanophenoxy)methyl-2-(5-cyanopyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 1594575
Notes
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Reaction equation

HRID 1594575 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:19][N:6]2[CH2:7][CH2:8][N:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][N:12]=3)[CH2:10][C@@H:5]2[CH2:4]1.[C:20]([C:22]1[CH:23]=[C:24](O)[CH:25]=[CH:26][CH:27]=1)#[N:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:20]([C:22]1[CH:27]=[C:26]([CH:25]=[CH:24][CH:23]=1)[O:1][CH2:2][C@@H:3]1[CH2:19][N:6]2[CH2:7][CH2:8][N:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][N:12]=3)[CH2:10][C@@H:5]2[CH2:4]1)#[N:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 133943-CyanophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22881891(7S,8aS)-7-hydroxymethyl-2-(5-cyanopyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

Product 1

HCID 70195483(7S,8aS)-7-(3-Cyanophenoxy)methyl-2-(5-cyanopyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine
Yield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (7S,8aS)-7-hydroxymethyl-2-(5-cyanopyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine, 1.6 g (13.4 mmol) of 3-cyanophenol, and 2.8 g (11 mmol) of triphenylphosphine were dissolved in 20 mL of dry THF, the solution was treated with 1.7 mL (11 mmol) of diethyl azodicarboxylate (DEAD), and the reaction stirred at ambient temperature for 16 hours. The solvent was evaporated, the residue taken up in ethyl acetate, and washed with 1M NaOH (sodium hydroxide). The organic phase was extracted with 1M HCl (3×), and the aqueous acid was washed with ethyl acetate (1×). The aqueous phase was made basic with 1M NaOH, extracted with ethyl acetate (3×), and the combined organic phase dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 75:25 ethyl acetate:hexane gave 0.603 g (19%) of the title compound. Mp (.HCl) 197-200° C. HRMS calc'd for C21H22N5O (MH+): 360.1824, found: 360.1802.

Workup

  1. customThe solvent was evaporated
  2. washwashed with 1M NaOH (sodium hydroxide)
  3. extractionThe organic phase was extracted with 1M HCl (3×)
  4. washthe aqueous acid was washed with ethyl acetate (1×)
  5. extractionextracted with ethyl acetate (3×)
  6. dry with materialthe combined organic phase dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by flash silica gel chromatography with 75:25 ethyl acetate

Sources & evidence

ORD record
ord-f058688fdbe441188115ad1b331c95b6
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06284757B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes