Acetyl chloride → HCID 58033730, compound

HRID 1873661Notes

Reaction equation

HRID 1873661 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 dropswise 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 was 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 was 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-5a1854c497c64aea8dc61946be70d513
Source dataset
uspto-grants-2012_11
Patent number
US08304423B2

Reaction notes

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