Hydroxyamine hydrochloride → tert-butyl 4-(hydroxyimino)-3,4-dihydro-2H-spiro[naphthalene-1,4'-piperidine]-1'-carboxylate

HRID 506543노트

반응식

HRID 506543 반응식
O=[C:2]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.Cl.[NH2:25][OH:26].O.O.O.C([O-])(=O)C.[Na+]>C(O)C>[OH:26][N:25]=[C:2]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate TrihydrateHCID 49760950Tert-butyl 4-oxo-3,4-dihydro-2H-spiro[naphthalene-1,4'-piperidine]-1'-carboxylate

생성물 1

HCID 86620083tert-butyl 4-(hydroxyimino)-3,4-dihydro-2H-spiro[naphthalene-1,4'-piperidine]-1'-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of tert-butyl 4-oxo-3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate A (1.24 g, 3.93 mmol), hydroxylamine hydrochloride (1.37 g, 19.7 mmol) and sodium acetate trihydrate (3.20 g, 23.5 mmol) in ethanol (50 ml) was heated under reflux for 20 h. The reaction was concentrated and the residue was suspended in water, extracted with dichloromethane (3×). The combined extracts were dried over Na2SO4 and concentrated to give tert-butyl 4-(hydroxyimino)-3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate B (1.32 g). LC-MS: m/e=331.1 (M+H, 100%), 275.0 (M+H−C(CH3)3). Rt=3.35 min. 1H-NMR (500 MHz, CDCl3): 8.01 (d, 0.25H), 7.93 (d, 0.75H), 7.41-7.34 (m, 2H), 7.23-7.19 (m, 1H), 3.95-3.92 (m, 2H), 3.04-2.96 (m, 2H), 2.87 (t, 0.5H), 2.82 (t, 1.5H), 2.3 (br. s, 1H), 1.93-1.84 (m, 4H), 1.54-1.52 (d, 2H), 1.43 (s, 9H).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. concentrationThe reaction was concentrated
  4. extractionextracted with dichloromethane (3×)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2dd5f4889c0e498197ff422bb844c9fa
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786107B2

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