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Sodium methanethiolate → (R)-3-((S)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 1261808
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HRID 1261808 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C@H:13]2[CH2:15][O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S-:17].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C@H:13]([OH:14])[CH2:15][S:17][CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

4

반응물 2

HCID 4378561Sodium methanethiolateHCID 86664073(R)-(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

생성물 1

HCID 66975342(R)-3-((S)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester수율 57%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

(R)-(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (1.0 g, 4.7 mmol, 1.0 eq.) in DMF (10 mL) was combined with sodium methyl mercaptide (2.5 g, 14.1 mmol, 3.0 eq.), and the resulting mixture was stirred at 50° C. for 3 hours under nitrogen. Upon completion of the reaction, the mixture was concentrated under vacuum, extracted with EtOAc, washed with saturated aqueous NaCl and water, dried, and concentrated. The crude product was purified by preparative HPLC (MeCN:EtOH=4:6) to yield the title compound (700 mg).

후처리

  1. customUpon completion of the reaction
  2. concentrationthe mixture was concentrated under vacuum
  3. extractionextracted with EtOAc
  4. washwashed with saturated aqueous NaCl and water
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative HPLC (MeCN:EtOH=4:6)

출처 및 근거

ORD 기록
ord-b039e8fc931c46d0b209182867bbc82b
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08471040B2

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