Hydroxyamine hydrochloride → 4-(N-t-Butyloxycarbonylpiperidin-4-ylmethoxy)benzaldoxime

HRID 1457712ノート

反応式

HRID 1457712 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:25][OH:26]>CO.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[N:25][OH:26])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 106393444-(N-t-Butyloxycarbonylpiperidin-4-ylmethoxy)benzaldehyde

生成物 1

HCID 851794404-(N-t-Butyloxycarbonylpiperidin-4-ylmethoxy)benzaldoxime収率 96.5%

試薬・触媒・溶媒 1

HCID 22021344Pyridine methanol溶媒

実験手順

A mixture of 4-(N-t-butyloxycarbonylpiperidin-4-ylmethoxy)benzaldehyde (3.16 g, 9.89 mmol) and hydroxylamine hydrochloride (1.27 g, 18.3 mmol) in 9:1 MeOH/pyridine (30 mL) was heated at reflux for 18 hours. The mixture was cooled to room temperature and concentrated to dryness. The residue was dissolved in EtOAc and washed with 0.1M HCl (3×), water, sat. CuSO4 (2×), water, sat. NaCl, dried (MgSO4) and concentrated, giving 3.19 g (96%) of the oxime; mp: 140.1°-141.8° C.; 1H NMR (300 MHz, CDCl3) δ 8.07 (s, 1H), 7.48 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 4.14 (bs, 2H), 3.80 (d, J=6.2 Hz, 2H), 2.71 (bt, J=12.4 Hz, 2H), 1.95 (m, 1H), 1.80 (bd, J=12.4 Hz, 2H), 1.45 (s, 9H), 1.26 (m, 2H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 0.1M HCl (3×), water, sat. CuSO4 (2×), water, sat. NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0f0d63f0860344f4b7e38d5fb561d8c1
出典データセット
uspto-grants-1998_12
特許番号
US05849736

反応ノート

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