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

HRID 276253

반응식

HRID 276253 반응식
[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

참가 물질

4

반응물 3

HCID 887MethanolHCID 2901CycloleucineHCID 24386Thionyl Chloride

생성물 1

HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HCl수율 100%

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1df1160096ee462089613b8be482eaf8
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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