Acetaldehyde → Tert-butyl 3-(ethylamino)pyrrolidine-1-carboxylate

HRID 242659

反応式

HRID 242659 の反応式
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[CH:14](=O)[CH3:15].[BH4-].[Na+]>CO>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][CH2:14][CH3:15])[CH2:3]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

参加物

5

反応物 3

HCID 177AcetaldehydeHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 4311764Sodium borohydride

生成物 1

HCID 20800658Tert-butyl 3-(ethylamino)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of (R)-3-amino-1-N-Boc pyrrolidine (1 eq, 5.37 mmol) in methanol (20 mL) was added acetaldehyde (0.95 eq) and the resulting mixture was heated to 80° C. and stirred for 2 h., then stirred at room temperature overnight. Sodium borohydride (0.95 eq, 5.1 mmol) was added and reaction mixture was stirred for an additional 2 h. The reaction mixture was concentrated, dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The combined organics were washed with brine and dried over sodium sulfate. The crude product was purified on silica using hexane/ethyl acetate (10%) to hexane/ethyl acetate (50%). 1H-NMR (CDCL3) δ: 1.05 (3H, t), 1.45 (9H, s), 1.60-1.75 (1H, m), 2.00-2.10 (1H, m), 2.68 (4H, q), 2.90-3.15 (1H, m), 3.25-3.65 (4H, m). ESI-MS m/z: 215 (M+1), UV retention time: 0.75 min.

後処理

  1. stirringstirred at room temperature overnight
  2. customreaction mixture
  3. stirringwas stirred for an additional 2 h
  4. concentrationThe reaction mixture was concentrated
  5. dissolutiondissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate
  7. washThe combined organics were washed with brine
  8. dry with materialdried over sodium sulfate
  9. customThe crude product was purified on silica

出典と根拠

ORDレコード
ord-6de36c0f01444b1d873210d6f2fcf513
出典データセット
uspto-grants-2014_02
特許番号
US08653096B2

関連ノート

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