{5-[3-(4-Trifluoromethyl-piperidin-1-yl)-propyl]-tricyclo [8.2.1.03,8]trideca-3(8),4,6-trien-13-yl}-carbamic Acid Tert-Butyl Ester → 5-[3-(4-Trifluoromethyl-piperidin-1-yl)-propyl]-tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-ylamine

HRID 722147Notes

Reaction equation

C(OC(=O)[NH:7][CH:8]1[CH:18]2[CH2:19][CH2:20][CH:9]1[CH2:10][C:11]1[CH:12]=[C:13]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH:27]([C:30]([F:33])([F:32])[F:31])[CH2:26][CH2:25]3)[CH:14]=[CH:15][C:16]=1[CH2:17]2)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:32][C:30]([F:31])([F:33])[CH:27]1[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][CH2:21][C:13]2[CH:14]=[CH:15][C:16]3[CH2:17][CH:18]4[CH:8]([NH2:7])[CH:9]([CH2:20][CH2:19]4)[CH2:10][C:11]=3[CH:12]=2)[CH2:25][CH2:26]1

Participants

Conditions

Temperature: 0 °C

Procedure

The Boc protecting group was removed by dissolving the product of Step 3 (87 mg, 0.181 mmol) in 3:1 DCM-TFA (4 ml) and stirring at 0° C. for 1 hour. The mixture was concentrated to dryness, and a solution of the residue in DCM washed with sodium carbonate solution (sat). The organic phase was dried and evaporated to give a colourless oil 66 mg (96%). 1H NMR (CDCl3, 360 MHz) δ 6.99 (1H, d, J=8.4 Hz), 6.90 (2H, m), 3.36 (1H, t, J=6.1 Hz), 3.21 (2H, m), 2.99 (2H, m), 2.45–2.59 (4H, m), 2.35 (2H, m), 2.23 (2H, m), 1.57–2.04 (11H, m), 1.17 (2H, m).

Workup

customThe Boc protecting group was removed
concentrationThe mixture was concentrated to dryness
washa solution of the residue in DCM washed with sodium carbonate solution (sat)
customThe organic phase was dried
customevaporated

Sources & evidence

ORD record: ord-d41bba33b086445a969b351ff79f4b92
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138400B2

Reaction notes

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