Sodium Hydroxide → 3-Hept-4-ylamino-8-t-butyl-1-oxaspiro(4,5)-decane

HRID 232556

反応式

HRID 232556 の反応式
[NH2:1][CH:2]1[CH2:6][C:5]2([CH2:11][CH2:10][CH:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:8][CH2:7]2)[O:4][CH2:3]1.[CH3:16][CH2:17][CH2:18][C:19](=O)[CH2:20][CH2:21][CH3:22].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[CH3:16][CH2:17][CH2:18][CH:19]([NH:1][CH:2]1[CH2:6][C:5]2([CH2:7][CH2:8][CH:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:10][CH2:11]2)[O:4][CH2:3]1)[CH2:20][CH2:21][CH3:22]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 312464-HeptanoneHCID 5003444Sodium cyanoborohydrideHCID 190401633-Amino-8-t-butyl-1-oxaspiro(4,5)-decane

生成物 1

HCID 190401523-Hept-4-ylamino-8-t-butyl-1-oxaspiro(4,5)-decane収率 72.4%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

To 3-amino-8-t-butyl-1-oxaspiro(4,5)-decane (1.12 g, 5 mmol) and heptane-4-one (0.6 g, 5.25 mmol) in dry methanol (20 ml) was added zinc chloride (0.41 g, 3 mmol). The mixture was stirred at room temperature for 5 minutes and sodium cyanoborohydride 0.38 g, 6 mmol) was added and the resulting heterogeneous mixture was stirred at room temperature overnight. The solvent was then stripped off in vacuo, toluene (50 ml) and 2N NaOH (50 ml) was added. The aqueous phase was extracted twice with toluene (2×50 ml) and the combined organic layers were dried (MgSO4) and concentrated in vacuo. The resulting oil was purified by flash chromatography to give a pale yellow oil (1.12 g). nD22 :1.4726.

後処理

  1. stirringthe resulting heterogeneous mixture was stirred at room temperature overnight
  2. additionwas added
  3. extractionThe aqueous phase was extracted twice with toluene (2×50 ml)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was purified by flash chromatography

出典と根拠

ORDレコード
ord-acfcef81c8034919b2eee27bae2f0bf5
出典データセット
uspto-grants-1997_01
特許番号
US05591741

関連ノート

読み込み中…