Methanol → Methyl 1-amino-1-cyclopentanecarboxylate, HCl

HRID 276253

反応式

HRID 276253 の反応式
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.O=S(Cl)[Cl:12].[CH3:14]O>>[ClH:12].[NH2:1][C:2]1([C:7]([O:9][CH3:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

4

反応物 3

HCID 887MethanolHCID 2901CycloleucineHCID 24386Thionyl Chloride

生成物 1

HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HCl収率 100%

実験手順

To a suspension of 1-aminocyclopentanecarboxylic acid, (675 g, 5.23 mol, 1.0 equiv.) in MeOH (6.5 L) held at −15° C. with an ice/MeOH bath was added SOCl2 (687 mL, 9.4 mol, 1.8 equiv.), dropwise at such a rate that the reaction temp. did not exceed 7° C. After the addition was complete, cooling was removed, the reaction was allowed to stir at room temp. overnight, then was concentrated under reduced pressure. The residue was treated with CH2Cl2 (1 L) and concentrated under reduced pressure to afford methyl 1-aminocyclopentanecarboxylate HCl salt as a white solid (938 g, 100%): 1H NMR (CD3OD) d 1.87-1.94 (m, 8H), 3.83 (s, 3H); NMR (DMSO-d6) δ1.67-1.71 (m, 2H), 1.83-1.98 (m, 4H), 2.06-2.14 (m, 2H), 3.73 (s, 3H), 8.81 (br s 3). This material was used in the next step without further purification.

後処理

  1. customheld at −15° C. with an ice/MeOH bath
  2. customdid not exceed 7° C
  3. additionAfter the addition
  4. temperaturecooling
  5. customwas removed
  6. concentrationwas concentrated under reduced pressure
  7. additionThe residue was treated with CH2Cl2 (1 L)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1df1160096ee462089613b8be482eaf8
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

関連ノート

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