Acetyl chloride → HCID 58033730, compound

HRID 1674723Notes

Reaction equation

HRID 1674723 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C@@H:6]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:9]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:8][CH2:7]1.C(N(CC)CC)C>C(#N)C>[C:1]([NH:5][C@@H:6]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:9]2([CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]2)[CH2:8][CH2:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58033755HCID 58033755, compound

Product 1

HCID 58033730HCID 58033730, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At −78° C., acetyl chloride (1 ml, 12 mmol) was added to a solution of the amine (B3) (3.2 g, 10 mmol) in dry acetonitrile (100 ml) followed by the dropwise addition of triethylamine. The reaction mixture was warmed to room temperature, stirred for 1 hour then concentrated. The residue was dissolved in ethyl acetate. The solution washed with saturated NaHCO3 and brine, dried and concentrated. The crude product was further purified by silica gel chromatography (CH2Cl2/CH3CN 9:1 to 7:3) to give (S)-tert-butyl 4-acetamido -3, 4-dihydro-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate (B4). LC-MS: m/e=359.3 (M+H), 303.3 (M+H−Me3CO). Rt=2.94 min. 1H-NMR (500 MHz, DMSO-d6): 8.17 (d, 1H), 7.36 (d, 1H), 7.22 (ddd, 1H), 7.14 (m, 2H), 4.95 (m, 1H), 3.86 (m, 2H), 2.97 (m, 2H), 2.01 (m, 1H), 1.85 (s, 3H), 1.80 (m, 4H), 1.61 (m 2H), 1.48 (d, 1H), 1.42 (s, 9H).

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution washed with saturated NaHCO3 and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was further purified by silica gel chromatography (CH2Cl2/CH3CN 9:1 to 7:3)

Sources & evidence

ORD record
ord-3591bdb7abb94db8a3c6cedf0d50ba39
Source dataset
uspto-grants-2011_08
Patent number
US08003660B2

Reaction notes

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