3-Pentanamine → Tert-butyl 3-(pentan-3-ylcarbamoyl)spiro[inden-1,4'-piperidine]-1'-carboxylate

HRID 2267115Notes

Reaction equation

HRID 2267115 reaction equation
[CH2:1]([CH:3]([NH2:6])[CH2:4][CH3:5])[CH3:2].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]2([C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([C:28](O)=[O:29])=[CH:20]2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH3:2][CH2:1][CH:3]([NH:6][C:28]([C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]2([CH2:18][CH2:19][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15][CH2:16]2)[CH:20]=1)=[O:29])[CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 120193-PentanamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 497602001'-(Tert-butoxycarbonyl)spiro[indene-1,4'-piperidine]-3-carboxylic acid

Product 1

HCID 59600632Tert-butyl 3-(pentan-3-ylcarbamoyl)spiro[inden-1,4'-piperidine]-1'-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-ethylpropylamine (0.5 mL) was added to a stirred solution of compound (C4) (0.50 g, 1.52 mmol), EDAC.HCl (0.6 g, 3.00 mmol), HOBt (0.31 g, 2.32 mmol) in DMF (10 mL) and the solution was stirred at room temperature for 2 h. The solution was poured into water (50 mL) and the aqueous layer was extracted with EtOAc (3×50 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by Biotage SP1 on silica gel eluting with 5-70% EtOAc in hexanes to provide tert-butyl 3-(pentan-3-ylcarbamoyl)spiro[inden-1,4′-piperidine]-1′-carboxylate (F1) as a white solid (0.6 g). LC/MS (10-90% over 3 min with 0.9% FA) m/z 399 (M+1), Rt 3.66 minutes. 1HNMR (500 MHz, DMSO-d6) δ 7.78 (d, 1H), 7.55 (m, 1H), 7.43 (d, 1H), 7.23 (br m, 1H), 4.07 (m, 2H), 3.75 (m,1H), 3.15 (m, 2H), 1.98 (d, 2H), 1.55 (m, 2H), 1.45 (s, 9H), 1.25 (m,2H), 0.88 (m, 6H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by Biotage SP1 on silica gel eluting with 5-70% EtOAc in hexanes

Sources & evidence

ORD record
ord-6e3893529d6245af9395725a23bdd9b2
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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