Trifluoroacetic acid → Trifluoroacetate
Reaction equation
BrC1C=CC=C2C=1C1(CCN(C(OC(C)(C)C)=O)CC1)CC2CC(OCC)=O.[Br:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:57]=1[C:37]1([CH2:42][CH2:41][N:40]([C:43](=[O:56])/[CH:44]=[CH:45]/[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:52]([F:55])([F:54])[F:53])[CH2:39][CH2:38]1)[CH2:36][CH:35]2[CH2:58][C:59]([OH:61])=[O:60].[C:62]([OH:68])([C:64]([F:67])([F:66])[F:65])=[O:63]>C(Cl)Cl>[Br:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:57]=1[C:37]1([CH2:38][CH2:39][N:40]([C:43](=[O:56])/[CH:44]=[CH:45]/[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:52]([F:53])([F:55])[F:54])[CH2:41][CH2:42]1)[CH2:36][CH:35]2[CH2:58][C:59]([OH:61])=[O:60].[F:65][C:64]([F:67])([F:66])[C:62]([O-:68])=[O:63]Participants
6
Reactant 3
Product 2
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl 7-bromo-3-(2-ethoxy-2-oxoethyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate isomer 1 (200 mg, 0.44 mmol) in anhydrous CH2Cl2 (2 mL) was added 20% TFA in CH2Cl2 (10 mL) at 0° C. The reaction mixture was stirred at rt for 1 h. The reaction mixture was concentrated to give ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate isomer 1 as its trifluoroacetate salt (156 mg, 100%), which was used to the next step without purification.
Workup
- concentrationThe reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-0eee2f73fe6e4f69bba991cca643e3e3
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383629B2
Reaction notes
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