Trifluoroacetic acid → HCID 66745343, compound

HRID 1959436Notes

Reaction equation

HRID 1959436 reaction equation
[CH:1]12[N:8](C(OC(C)(C)C)=O)[CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:16]([O:18][CH2:19][CH:20]1[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:26]3[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[CH2:2]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:5]12[NH:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:16]([O:18][CH2:19][CH:20]1[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:26]3[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[CH2:4]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66744271HCID 66744271, compound

Product 1

HCID 66745343HCID 66745343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(9H-fluoren-9-yl)methyl 8-tert-butyl 3,8-diazabicyclo[3.2.1]octane-3,8-dicarboxylate in DCM (2 mL) from the step 1 was treated dropwise with TFA (2.2 g, 1.5 mL, 19.5 mmol) at room temperature and the reaction mixture was stirred for 1 h. The solvents were removed under reduced pressure and the crude material was dissolved in 1 N HCl (2 mL) and washed with ether. The solution was basified with saturated bicarbonate solution and the aqueous layer was extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated to obtain a solution of (9H-fluoren-9-yl)methyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate in DCM (2 mL), which was used directly for the next step. LC/MS m/z 335.5 [M+H]+.

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe crude material was dissolved in 1 N HCl (2 mL)
  3. washwashed with ether
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-37068f112dc64043af9ffdc7801d09ad
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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