Acetic Acid → Nadolol

HRID 1109312

반응식

HRID 1109312 반응식
C(N)(C)(C)C.[C:6]([NH:10][CH2:11][CH:12]([OH:25])[CH2:13][O:14][C:15]1[C:24]2[CH2:23][CH:22]=CC[C:19]=2[CH:18]=[CH:17][CH:16]=1)([CH3:9])([CH3:8])[CH3:7].[C:26]([O:29]I)(=O)[CH3:27].C(O)(=[O:33])C>[Ag]I>[CH3:7][C:6]([NH:10][CH2:11][CH:12]([OH:25])[CH2:13][O:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[CH2:27][C@@H:26]([OH:29])[C@@H:22]([OH:33])[CH2:23][C:24]=12)([CH3:9])[CH3:8]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6385Tert-ButylamineHCID 11087015HCID 11087015, 화합물HCID 11446761HCID 11446761, 화합물

생성물 1

HCID 39147Nadolol

시약·촉매·용매 1

HCID 24563Silver iodide촉매

실험 절차

Subsequently Hauck in Canadian Letters Patent 1,041,544 attempted to separate the four optical cis isomers of 2,3-cis-1,2,3,4-tetrahydro-S-[2-hydroxy-3-(tert-butylamino) propoxy]-2,3-naphthalenediol in order to determine the best of these isomers. The processes of manufacture (See pages 4, 5 and 6 of the Patent and example 4 at pages 18 and of the patent) employ water. Crystallization of isomer product is from chloroform. In Hauck's laboratory procedure resulting 1-(2,3-epoxypropoxy)-5,8-dihydronaphthalene is isolated and subsequently reacted with t-butylamine in a high pressure reactor. The resulting dl-1-(tert-butylamino)-3-(5,8-dihydronaphthyl)oxyl-2-propanol is then cis hydroxylated with wet acetic acid, silver iodide, and the resulting acetoxy iodide is hydrolysed with base and finally subjected to catalytic hydrogenation to afford crude Nadolol.

후처리

  1. customis isolated

출처 및 근거

ORD 기록
ord-26ef28bfcba64683971d76ca8f18c42a
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05319141

연결된 노트

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