L-Alaninol → HCID 58743044、化合物

HRID 714594ノート

反応式

HRID 714594 の反応式
CS(O[CH2:6][C@H:7]([CH3:15])[CH2:8][CH2:9]OS(C)(=O)=O)(=O)=O.[NH2:16][C@@H:17]([CH3:20])[CH2:18][OH:19]>C(Cl)Cl.C([O-])([O-])=O.[K+].[K+].O>[CH3:15][C@@H:7]1[CH2:8][CH2:9][N:16]([C@@H:17]([CH3:20])[CH2:18][OH:19])[CH2:6]1

参加物

6

反応物 2

HCID 80307L-AlaninolHCID 10858216HCID 10858216、化合物

生成物 1

HCID 58743044HCID 58743044、化合物収率 86.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 11430Potassium Carbonate溶媒

実験手順

(R)-2-Methylbutane-1,4-diyl dimethanesulfonate (37.5 g, 0.144 mol) was added to neat (S)-2-aminopropan-1-ol (54.8 g, 0.730 mol). The mixture was stirred in a room temperature water bath to minimize the exotherm. After 24 h, the reaction was diluted with DCM (150 mL), saturated aqueous K2CO3 solution (150 mL), and enough water (60 mL) to dissolve the resulting precipitate. The organic layer was separated and the aqueous layer was extracted with DCM (150 mL). The organic layers were combined, dried over (Na2SO4), filtered, concentrated, and purified by silica gel chromatography (10:7; ethyl acetate:hexanes→10:7:2:1; ethyl acetate:hexanes:methanol:triethylamine) to give (S)-2-((R)-3-methylpyrrolidin-1-yl)propan-1-ol (17.9 g) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 4.33 (t, 1H), 3.48 (m, 1H), 3.18 (m, 1H), 2.79 (dd, 1H), 2.58 (m, 1H), 2.48 (m, 1H), 2.26 (m, 1H), 2.08 (m, 1H), 2.01 (dd, 1H), 1.88 (m, 1H), 1.20 (m, 1H), 0.98 (d, 3H), 0.96 (d, 3H); LCMS: 144.3 (M+H)+.

後処理

  1. dissolutionto dissolve the resulting precipitate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (150 mL)
  4. dry with materialdried over (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (10:7; ethyl acetate:hexanes→10:7:2:1; ethyl acetate:hexanes:methanol:triethylamine)

出典と根拠

ORDレコード
ord-7983e327d18c44ac9984fe6c54d5623d
出典データセット
uspto-grants-2015_11
特許番号
US09187460B2

反応ノート

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