Methanesulfonyl chloride → tert-butyl (2R,4S)-4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate

HRID 384503노트

반응식

HRID 384503 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:10][C@@H:9]1[CH2:14][O:15][S:17]([CH3:16])(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 4204845Tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 86629965tert-butyl (2R,4S)-4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (10.85 g, 50.0 mmol) in pyridine (50 mL) was added methanesulfonyl chloride (10.8 mL, 140 mmol) over a period of 20 min. After stirring for 16 h, the reaction mixture was concentrated to dryness, diluted with satd. aq. Na2CO3 and extracted with EtOAc (2×). The combined organic layers were dried (MgSO4), filtered and concentrated to provide the title compound as an oil that slowly solidified (14.4 g, 84%). 1H NMR (400 MHz, CDCl3): 5.24-5.20 (m, 1H), 4.72-4.47 (m, 1H), 4.32-4.17 (m, 2H), 4.01-3.75 (m, 1H), 3.63-3.48 (m, 1H), 3.04 (s, 3H), 3.01 (s, 3H), 2.60-2.25 (m, 2H), 1.48 (s, 9H).

후처리

  1. concentrationthe reaction mixture was concentrated to dryness
  2. additiondiluted with satd
  3. extractionaq. Na2CO3 and extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e969420556e54b0585dcbd760e75d9f7
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367719B2

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