Sodium Hydroxide → (3S,4S)-1-Boc-4-methyl-piperidine-3-carboxylic acid

HRID 931303노트

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HRID 931303 반응식
[OH-].[Na+].[CH3:3][C@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@H:5]1[C:17]([O:19]CC)=[O:18]>CO>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C@H:4]([CH3:3])[C@H:5]([C:17]([OH:19])=[O:18])[CH2:6]1)=[O:11])([CH3:14])([CH3:15])[CH3:16]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 131735164cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

생성물 1

HCID 86317483(3S,4S)-1-Boc-4-methyl-piperidine-3-carboxylic acid수율 98.2%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

An aqueous solution of sodium hydroxide (2N, 20 mL) was added to a solution of cis-1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (2.5 g, 9.21 mmol) in methanol (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 h. The solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was acidified to pH 2 using aqueous hydrochloric acid (1N) and was extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford cis-1-(tert-butoxycarbonyl)-4-methylpiperidine-3-carboxylic acid (2.2 g).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ede4e7d96faf4eb1aeb1eb37ca53e5a8
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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