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

HRID 232556

반응식

HRID 232556 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-acfcef81c8034919b2eee27bae2f0bf5
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591741

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