Trifluoroacetic acid → N-(2-adamantyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 1424586Notes

Reaction equation

[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21](C(OC(C)(C)C)=O)[CH2:20]3)[CH2:16][CH2:15]1)=[O:13])[CH2:8]2.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:15][CH2:16][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH2:20]3)[CH2:18][CH2:19]1)=[O:13])[CH2:8]2

Participants

Conditions

Temperature: 0 °C

Procedure

A 10-mL round-bottomed flask was charged with tert-butyl 1′-((2-adamantyl)carbamoyl)spiro[indoline-3,4′-piperidine]-1-carboxylate (50 mg, 0.107 mmol) and 20% trifluoroacetic acid in CH2Cl2 (2 mL). The mixture was stirred for 1 h at 0° C. The solution was concentrated under vacuum and the crude product was purified by preparative HPLC to provide N-(2-adamantyl)spiro[indoline-3,4′-piperidine]-1′-carboxamide (10 mg, 25%). 1H NMR (CD3OD, 400 MHz): δ=1.60˜2.00 (m, 18H), 3.00 (t, 2H), 3.86 (d, 3H), 4.08 (d, 2H), 7.40˜7.50 (m, 4H); LC-MS (4 min) tR=1.93 min, m/z=366 (M++1).

Workup

concentrationThe solution was concentrated under vacuum
customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-49b922e338ec4c81b4e8dc8de679fcb2
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927715B2

Reaction notes

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