Hydrochloric Acid → 1-(tert-Butoxycarbonyl)-4-[(4-chlorophenyl)methyl]piperidine-4-carboxylic acid

HRID 1470263ノート

反応式

HRID 1470263 の反応式
C[O:2][C:3]([C:5]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].O.[OH-].[Li+].Cl>O1CCOCC1.CO.O>[C:14]([O:13][C:11]([N:8]1[CH2:7][CH2:6][C:5]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 598404671-(1,1-Dimethylethyl) 4-methyl 4-[(4-chlorophenyl)methyl]-1,4-piperidinedicarboxylate

生成物 1

HCID 189689961-(tert-Butoxycarbonyl)-4-[(4-chlorophenyl)methyl]piperidine-4-carboxylic acid収率 100.2%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

To a solution of 4-(4-chlorobenzyl)piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.515 g, 4.117 mmol) in dioxane (20 ml), methanol (10 ml) and water (10 ml) at room temperature was added lithium hydroxide monohydrate (3.455 g, 82.341 mmol). After stirring at 50° C. for 2 days the solution was acidified to pH 6 with 2M HCl and the resulting white precipitate was extracted with diethyl ether (2×100 ml). The organic phases were combined, dried over sodium sulphate and concentrated to dryness, to give the acid as a white solid (1.460 g, 100%). LC-MS (LCT) m/z 376 [M+Na+], Rt 7.62 min.

後処理

  1. extractionthe resulting white precipitate was extracted with diethyl ether (2×100 ml)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-4a13196dbf704091955137ee9bfa06ff
出典データセット
uspto-grants-2015_04
特許番号
US09006430B2

反応ノート

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