Hydrochloric Acid → Benzyl 4-(methoxycarbonylamino)piperidine-1-carboxylate

HRID 369110

反応式

HRID 369110 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]=[C:18]=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:20].Cl.[CH3:22]O>CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][CH3:22])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 2776273Benzyl 4-isocyanatopiperidine-1-carboxylate

生成物 1

HCID 18677680Benzyl 4-(methoxycarbonylamino)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

実験手順

To a solution of 1.0 g (3.9 mmol) of (1-benzyloxycarbonyl-piperidin-4-yl)isocyanate from Example 64, Step A in 10 mL of methanol was added 5 mg (cat) of DMAP. The reaction was stirred under nitrogen at rt for 24 h and then poured into water containing 2 mL of 2 N hydrochloric acid and was extracted twice with ethyl acetate. The organic layers were each washed with a portion of brine, dried over sodium sulfate, combined and concentrated to give 1.4 g of the crude title compound which can be used directly in subsequent reactions. 1H NMR (400 MHz, CDCl3): δ 1.32 (m, 2H), 1.92 (br d, J=10, 4H), 2.91 (v br t, 2H), 3.66 (br s, 3H+1H), 4.10 (m, 2H), 4.58 (br s, 1H), 5.09 (s, 2H), 7.33 (m, 5H).

後処理

  1. extractionwas extracted twice with ethyl acetate
  2. washeach washed with a portion of brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-6ef14d10d6994e19923301ee997b5f97
出典データセット
uspto-grants-2000_10
特許番号
US06136827

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