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

HRID 1808707ノート

反応式

HRID 1808707 の反応式
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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887Methanol2 回HCID 3939Lithium HydroxideHCID 707916011-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f99dfc6952de45fd920a9ba89c447e36
出典データセット
uspto-grants-2013_01
特許番号
US08361962B2

反応ノート

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