tert-butyl (3R)-3-aminopiperidine-1-carboxylate → HCID 89554205, compound

HRID 1507487Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[C:12]([N:19]1[CH2:24][CH2:23][CH2:22][C@@H:21]([NH2:25])[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C(O)C>[CH3:9][O:8][C:6]1[N:5]=[C:4]([S:10][CH3:11])[N:3]=[C:2]([NH:25][C@@H:21]2[CH2:22][CH2:23][CH2:24][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20]2)[CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Compound 2 (3.6 g, 18.9 mmol) and (R)-1-Boc-3-aminopiperidine (9.45 g, 47.2 mmol) were dissolved in ethanol (50 mL) and TEA (10.5 mL, 76 mmol) was added. The reaction was sealed and heated to 130° C. for 72 h. The orange solution was concentrated and the residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give the title compound as a white foam. 1H NMR (CDCl3) δ 5.40 (s, 1H), 4.78 (br s, 1H), 3.88 (s, 3H), 3.84-3.81 (m, 1H), 3.58-3.56 (m, 2H), 3.17-3.05 (m, 2H), 2.49 (s, 3H), 2.04-1.91 (m, 1H), 1.75-1.67 (m, 1H), 1.57-1.51 (m, 2H), 1.44 (s, 9H); LCMS 2.30 min, 355 (M+H).

Workup

customThe reaction was sealed
concentrationThe orange solution was concentrated
customthe residue was purified by column chromatography on silica gel
washeluting with EtOAc/hexane

Sources & evidence

ORD record: ord-751662a0496e490db449d441138d17f9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221809B2

Reaction notes

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