Trityl chloride → N-trityl-1-hydroxytricyclo[3.3.1.13,7]decan-2-amine

HRID 234745

반응식

HRID 234745 반응식
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH2:12])[CH2:9]2.[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[C:19]([NH:12][CH:3]1[CH:4]2[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][C:2]1([OH:1])[CH2:11]3)[CH2:10]2)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

4

반응물 2

HCID 6456Trityl chloride2회HCID 124667122-Aminoadamantan-1-ol

생성물 1

HCID 54340516N-trityl-1-hydroxytricyclo[3.3.1.13,7]decan-2-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To 1-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (0.47 g; 0.0028 mole), [prepared via a procedure of W. V. Curran and R. B. Angier, J. of Org. Chem., 34(11), 3668-70 (1969)] in dichloromethane (45 ml)is added triphenylmethyl chloride (0.78 g; 0.0028 mole) in dichloromethane (5 ml). This mixture is refluxed for 7 hours and then more triphenylmethyl chloride (0.35 g) is added and the reaction refluxed overnight. The reaction is stripped to dryness and the products separated via flash chromatography (eluted with 25% ethyl acetate/hexane) to obtain N-trityl-1-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine which is used directly in step B.

후처리

  1. temperatureThis mixture is refluxed for 7 hours
  2. temperaturethe reaction refluxed overnight
  3. customthe products separated via flash chromatography (eluted with 25% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-5aacd6119b2f466d9ff0e62f15ad79b8
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05596020

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