Methanol → HCID 22235386, compound

HRID 1743718Notes

Reaction equation

HRID 1743718 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=2)[CH2:10][CH2:11][CH2:12][N:13]2[CH2:19][CH:18]3[N:20](C(OC(C)(C)C)=[O:22])[CH:15]([CH2:16][CH2:17]3)[CH2:14]2)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[NH4+:2].[OH-:22].[CH:18]12[NH:20][CH:15]([CH2:16][CH2:17]1)[CH2:14][N:13]([CH2:12][CH2:11][CH2:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[O:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1)[CH2:19]2

Participants

6

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 22235448HCID 22235448, compound

Product 2

HCID 14923Ammonium HydroxideHCID 22235386HCID 22235386, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 3-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (17.3 g, 33.2 mmol; from step (a) above) in CH2Cl2 (600 mL) was added TFA (130 mL). The resulting solution was stirred for 30 min then concentrated in vacuo. The residue was neutralized with aqueous Na2CO3, extracted with CH2Cl2 (3×), dried (Na2SO4), filtered and concentrated in vacuo to give an oil. Flash chromatography on silica gel eluting with CH2Cl2:MeOH:concentrated NH4OH (177:20:3) gave 5.0 g (36%) of the title compound as an oil.

Workup

  1. concentrationthen concentrated in vacuo
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil

Sources & evidence

ORD record
ord-5f24f3e8c2d649bba5bb6453321d0ac0
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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