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

HRID 931303ノート

反応式

HRID 931303 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ede4e7d96faf4eb1aeb1eb37ca53e5a8
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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