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

HRID 1159417

反応式

HRID 1159417 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-09321d21e421469b9219d218e93c6239
出典データセット
uspto-grants-2010_10
特許番号
US07812040B2

関連ノート

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