Pyrrolidine → 3-Methyl-4-(pyrrolidin-1-ylmethyl)phenol

HRID 1159417

반응식

HRID 1159417 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[CH:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].OS([O-])(=O)=O.[Na+]>C(Cl)Cl.O>[CH3:10][C:4]1[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][C:5]=1[CH2:6][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

참가 물질

7

반응물 4

HCID 31268PyrrolidineHCID 4581854-Hydroxy-2-methylbenzaldehydeHCID 516919Sodium BisulfateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 686199283-Methyl-4-(pyrrolidin-1-ylmethyl)phenol수율 94.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

4-Hydroxy-2-methylbenzaldehyde (1.1 g, 8 mmol) was added in portions for 30 min to a mixture of pyrrolidine (0.84 mL, 10 mmol) and NaB(OAc)3H (2.14 g, 10 mmol) in CH2Cl2 (10 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon. The mixture was stirred for 12 h and cooled with an ice bath. Water (20 mL) and 5N NaHSO4 (to pH 1) were added. The organic layer was separated and discarded. The aqueous one was alkalized with saturated K2CO3 to pH 6 and extracted with chloroform (2×25 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compound (1.45 g, 94%) was obtained as dark-yellow crystals. LCMS-data: (M+H)+ 193.1 and 192.1 (calculated for C12H17NO 191.3). 1H NMR data (DMSO-d6): 9.08 (br. s, 1H ArOH), 6.97 (d, 1H, J=8.1 Hz, Ar—H), 6.54 (d, 1H, J=2.4 Hz, Ar—H); 6.49 (dd, 1H, J1=2.4 Hz, J2=8.1 Hz, Ar—H), 3.40 (s, 2H, ArCH2), 2.33-2.45 (m, 4H, pyrrolidine (CH2)2N),), 2.21 (s, 3H, OCH3), 1.60-1.68 (m, 4H, CH2CH2CH2CH2).

후처리

  1. temperaturecooling with an ice bath in an atmosphere of argon
  2. stirringThe mixture was stirred for 12 h
  3. temperaturecooled with an ice bath
  4. customThe organic layer was separated
  5. extractionextracted with chloroform (2×25 mL)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-09321d21e421469b9219d218e93c6239
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812040B2

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