Sodium Carbonate → 1-{[(9H-Fluoren-9-yl)methoxy]carbonyl}piperidine-2-carboxylic acid

HRID 2277083노트

반응식

HRID 2277083 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].C([O-])([O-])=O.[Na+].[Na+].[C:16](Cl)([O:18][CH2:19][CH:20]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17]>O.O1CCOCC1>[CH:31]1[C:32]2[CH:20]([CH2:19][O:18][C:16]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]3[C:7]([OH:9])=[O:8])=[O:17])[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]=2[CH:28]=[CH:29][CH:30]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 439227Pipecolic acid, (-)-

생성물 1

HCID 9830421-{[(9H-Fluoren-9-yl)methoxy]carbonyl}piperidine-2-carboxylic acid수율 51.8%

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

To a stirred mixture of (S)-piperidine-2-carboxylic acid (1.0 g, 7.75 mmol) and Na2CO3 (1.65 g, 15.50 mmol) in water (10 mL) was added a solution of FMOC-Cl (3.0 g, 11.63 mmol) in 1,4-dioxane (10 mL) dropwise at 0° C. and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water (50 mL) and washed with MTBE (25 mL). The aqueous layer was acidified with 1M aqueous HCl (10 mL) to pH 2 and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine solution (50 mL), dried over anhydrous Na2SO4, filtered and concentrated to afford the title compound (1.41 g) as an off-white solid. The crude product was used in the next step without purification.

후처리

  1. washwashed with MTBE (25 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic extracts were washed with brine solution (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2632b96561a14d9896ea80dce9257ba5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133147B2

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