Sodium Hydroxide → 4-(3,4-Dichlorophenoxy)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

HRID 1060803노트

반응식

HRID 1060803 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[C:16]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl.C(OCC)C.C(O)(=O)C>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][CH:26]([N:9]2[CH2:10][CH2:11][CH:6]([O:5][C:4]3[CH:12]=[CH:13][C:14]([Cl:15])=[C:2]([Cl:1])[CH:3]=3)[CH2:7][CH2:8]2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 112125444-(3,4-Dichlorophenoxy)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매HCID 3283Diethyl Ether용매

실험 절차

4-(3,4-Dichlorophenoxy)piperidine (1.5 g) was dissolved in 1,2-dichloroethane (21 ml). 1-Boc-4-piperidone was added (1.21 g) followed by NaBH(OAc)3 (1.81 g) and acetic acid (0.37 g). After 18 hours at room temperature aqueous NaOH (1M) solution and diethyl ether were added. The product was extracted with diethyl ether, the combined organic extracts dried with MgSO4 and concentrated. Purification by silica chromatography (dichloromethane:methanol 92:8) gave the sub-title product (1.97 g).

후처리

  1. extractionThe product was extracted with diethyl ether
  2. dry with materialthe combined organic extracts dried with MgSO4
  3. concentrationconcentrated
  4. customPurification by silica chromatography (dichloromethane:methanol 92:8)

출처 및 근거

ORD 기록
ord-320b3a82f4824c168b3c4f31b308eff3
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525070B2

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