Triethylamine → (R)-tert-butyl 3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate

HRID 931179노트

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HRID 931179 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([C:19](O)=[O:20])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C)C=O>[N:1]1([C:19]([C@@H:15]2[CH2:16][CH2:17][CH2:18][N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH2:14]2)=[O:20])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 28167609(R)-tert-butyl 3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
30 °C

실험 절차

To a solution of pyrrolidine (2.134 g, 30 mmol) in N,N-dimethylformamide (240 mL) was added (R)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (6.878 g, 30 mmol). Then hydroxybenzotriazole (1.028 g, 6 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (5.751 g, 30 mmol), and triethylamine (7.59 g, 75 mmol) were added sequentially. The mixture was stirred at 30° C. for 16 h. The solvent was removed under reduced pressure and an aqueous solution of sodium bicarbonate (200 mL, 0.1M) was added. The mixture was extracted with ethyl acetate (200 mL×3) and the combined organics were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford (R)-tert-butyl 3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate, which was used in the next step without further purification.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionan aqueous solution of sodium bicarbonate (200 mL, 0.1M) was added
  3. extractionThe mixture was extracted with ethyl acetate (200 mL×3)
  4. dry with materialthe combined organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-66b90b7ff3f24923b388fe9df1a315c1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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