Hydrochloric Acid → trans-1-Tert-butoxycarbonyl-4-methyl-piperidine-3-carboxylic acid

HRID 1808707노트

반응식

HRID 1808707 반응식
C([O:3][C:4]([CH:6]1[CH:11]([CH3:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=[O:5])C.CO.[OH-].[Li+].Cl>O1CCCC1>[C:16]([O:15][C:13]([N:8]1[CH2:9][CH2:10][C@@H:11]([CH3:12])[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 887Methanol2회HCID 3939Lithium HydroxideHCID 707916011-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

생성물 1

HCID 86317481trans-1-Tert-butoxycarbonyl-4-methyl-piperidine-3-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a flask containing (+/−)-4-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.12 g, 4.1 mmol; from example 8 above) was taken up in tetrahydrofuran (12 mL) and methanol (3 mL) and cooled to 0° C. (ice bath). A solution of lithium hydroxide (4.5 mL, 1M) was added and the mixture was warmed to ambient over 3 hours. Extra methanol (2 mL) was added and the material was heated to 60° C. (oil bath) for 5.5 hours. The mixture was cooled to ambient and treated with 1N hydrochloric acid solution (4.7 mL) with vigorous stirring. The solvent was stripped and the remainder was dried under high vacuum for several hours, providing 1.06 g of mainly trans-(+/−)-4-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester: as a off-white solid. MS (M−H)−=242.

후처리

  1. temperaturethe mixture was warmed
  2. temperatureThe mixture was cooled to ambient and
  3. customthe remainder was dried under high vacuum for several hours

출처 및 근거

ORD 기록
ord-f99dfc6952de45fd920a9ba89c447e36
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08361962B2

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