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

HRID 242659

반응식

HRID 242659 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6de36c0f01444b1d873210d6f2fcf513
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653096B2

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