(R)-Benzyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate → (R)-Pyrrolidin-2-YL-pyrrolidin-1-YL-methanone

HRID 1766748

반응식

HRID 1766748 반응식
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17])=O)C1C=CC=CC=1>CO.[Pd]>[N:18]1([C:16]([C@H:12]2[CH2:13][CH2:14][CH2:15][NH:11]2)=[O:17])[CH2:19][CH2:20][CH2:21][CH2:22]1

참가 물질

4

반응물 1

HCID 667614(R)-Benzyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

생성물 1

HCID 10034997(R)-Pyrrolidin-2-YL-pyrrolidin-1-YL-methanone

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of (+)-carbobenzyloxy-D-proline (1.5 g, 6 mmol), EDC (2.3 g, 12 mmol), HOBt (800 mg, 6 mmol), TEA (1.5 mL) and pyrrolidine (853 mg, 12 mmol) in DMF (20 mL) was stirred at rt for 18 hr. The reaction was diluted with water and sodium bicarbonate, extracted with dichloromethane (3×). The combined DCM was concentrated and purified on a silica gel column to give (R)-2-(pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester. (R)-2-(pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester was hydrogenated using Pd/C in methanol at ambient temperature for 20 hr to provide pyrrolidin-1-yl-(R)-pyrrolidin-2-yl-methanone. To a solution of pyrrolidin-1-yl-(R)-pyrrolidin-2-yl-methanone (1.2 g, 7.1 mmol) in THF (10 mL) at 0° C. was added B2H6 (10 mL, 10 mmol). The mixture was heated to reflux for 16 hr. The reaction was acidified with HCl and concentrated. The residue was basified to pH 10 with 2N NaOH and extracted with 5% methanol in DCM. The organic layer was concentrated and purified on a silica gel column to give 800 mg (73%) of (R)-2-pyrrolidin-1-ylmethyl-pyrrolidine.

후처리

  1. customat ambient temperature
  2. customfor 20 hr

출처 및 근거

ORD 기록
ord-e4a74190195f45e08717ad28cf44ac3c
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230098B2

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