tert-Butyl carbamate → (1'-benzyl-1-(5-ethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4'-piperidine]-4-yl)methanamine tris(2,2,2-trifluoroacetate)
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][NH:23]C(=O)OC(C)(C)C)[N:15]([C:31]3[C:32]4[CH:39]([CH2:40][CH3:41])[CH2:38][CH2:37][C:33]=4[N:34]=[CH:35][N:36]=3)[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N)(OC(C)(C)C)=O.[C:50]([OH:56])([C:52]([F:55])([F:54])[F:53])=[O:51].C(Cl)Cl>>[F:53][C:52]([F:55])([F:54])[C:50]([OH:56])=[O:51].[F:53][C:52]([F:55])([F:54])[C:50]([OH:56])=[O:51].[F:53][C:52]([F:55])([F:54])[C:50]([OH:56])=[O:51].[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][NH2:23])[N:15]([C:31]3[C:32]4[CH:39]([CH2:40][CH3:41])[CH2:38][CH2:37][C:33]=4[N:34]=[CH:35][N:36]=3)[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 3
Product 1
Procedure
tert-Butyl (1′-benzyl-1-(5-ethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methylcarbamate (422 mg, 0.762 mmol) was dissolved in a 1:1 TFA/DCM solution (10 mL). After 2 hours at room temperature, the LCMS suggested complete deprotection of the BOC amine. The reaction was concentrated to (1′-benzyl-1-(5-ethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methanamine tris(2,2,2-trifluoroacetate) (606 mg, 0.762 mmol, 99.9% yield) as an oil. MS (APCI+) [M+H]: 454.2.
Sources & evidence
- ORD record
- ord-af36d7d612764fc5a2a4fc019a5b806a
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346805B2
Reaction notes
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