Triethylamine → HCID 59656454, compound

HRID 1726494Notes

Reaction equation

HRID 1726494 reaction equation
[F:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([S:12](Cl)(=[O:14])=[O:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C1COCC1.ClCCl>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([NH:36][S:12]([C:5]2[C:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=3[C:2]([F:1])=[CH:3][CH:4]=2)(=[O:14])=[O:13])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 55279082HCID 55279082, compound

Product 1

HCID 59656454HCID 59656454, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Fluoro-5,6,7,8-tetrahydro-naphthalene-1-sulfonyl chloride (860 mg, 3.46 mmol) was dissolved in THF (10 mL). Triethylamine (350 mg, 0.49 mg, 3.46 mmol) was added, followed by 4-amino-piperidine-1-carboxylic acid tert-butyl ester (694 mg, 3.46 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was diluted with dichloromethane (50 mnL) and charged to a separatory funnel. The organic layer was washed with water and brine, then dried over MgSO4. Filtration and concentration in vacuo afforded a yellow foam. Wt.: 1.35 g (95%). 1H NMR (300 MHz, CDCl3) δ 7.88 (dd, 1H), 6.95 (t, 1H), 4.47 (d, 1H), 3.93 (m, 2H), 3.27 (m, 1H), 3.11 (m, 2H), 2.76 (m, 4H), 1.81 (m, 6H), 1.44 (s, 9H), 1.32 (m, 2H); LC/MS m/z 411 (M−H)−.

Workup

  1. additioncharged to a separatory funnel
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and concentration in vacuo
  5. customafforded a yellow foam

Sources & evidence

ORD record
ord-cb2d4b26c22240439e78f8c2dd326ef2
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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