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

HRID 1470263노트

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HRID 1470263 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
50 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4a13196dbf704091955137ee9bfa06ff
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006430B2

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