Piperidine → HCID 70803885, compound

HRID 2179800Notes

Reaction equation

HRID 2179800 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([OH:15])=O)[C:10]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18]1[CH:19]=[CH:20]C2N(O)N=[N:24][C:22]=2[CH:23]=1.N1CCCCC1.CCN(CC)CC>C(Cl)Cl>[CH3:16][C:10]1([CH3:17])[C@@H:11]([C:13]([N:24]2[CH2:20][CH2:19][CH2:18][CH2:23][CH2:22]2)=[O:15])[CH2:12][C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 15819069HCID 15819069, compound

Product 1

HCID 70803885HCID 70803885, compoundYield 62.79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (1S,3R)-3-(tert-butoxycarbonylamino)-2,2-dimethylcyclobutanecarboxylic acid (0.500 g, 2.057 mmol) in DCM (20 ml) EDCI (0.472 g, 2.469 mmol) and HOBt (0.378 g, 2.469 mmol) were added at 0° C. and after 10 minutes, piperidine (0.4 ml, 4.115 mmol) and Et3N (1.42 ml, 10.288 mmol) were added drop wise and the reaction mass was allowed to stir at room temperature for about 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with DCM and washed with water, sat. NaHCO3 solution, water, 1N HCl, water, saturated brine and the organic layer was concentrated under reduced pressure, the resulting crude residue was stirred in hexane and the resulting solid was obtained which was filtered and dried under vacuum to afford the title compound. Wt: 0.400 g; Yield: 62.79%; 1H NMR (300 MHz, CDCl3): δ 4.77 (d, 1H, J=8.4 Hz), 3.89-3.78 (m, 1H), 3.77-3.67 (m, 1H), 3.49-3.28 (m, 3H), 2.87-2.76 (m, 1H), 2.40-2.18 (m, 2H), 1.70-1.46 (m, 6H), 1.43 (s, 9H), 1.33 (s, 3H), 0.87 (s, 3H); Mass: [M+1]+ 311 (35%), [M+Na]+ 333 (100%); IR (KBr, cm−1): 3337, 2939, 1712, 1628, 1522, 1456, 1445, 1388, 1353, 1366, 1288, 1264, 1254, 1217, 1172, 1047, 1026, 1013, 976; M.R: 176.0° C.-178.0° C.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. washwashed with water, sat. NaHCO3 solution, water, 1N HCl, water, saturated brine
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. stirringthe resulting crude residue was stirred in hexane
  5. customthe resulting solid was obtained which
  6. filtrationwas filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b5d6db6ffb774751877e4b783bb8fdeb
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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