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Water → 4-Azido-2-methoxymethyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

HRID 1071493
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HRID 1071493 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH:9]1[CH2:18][O:19][CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+].O.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:21]=[N+:22]=[N-:23])[CH2:10][CH:9]1[CH2:18][O:19][CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

6

반응물 4

HCID 962WaterHCID 33557Sodium AzideHCID 199002664-Methanesulfonyloxy-2-methoxymethyl-pyrrolidine-1-carboxylic Acid T-butyl EsterHCID 21226206Ethyl acetate hexane

생성물 1

HCID 865852374-Azido-2-methoxymethyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

The 4-methanesulfonyloxy-2-methoxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester (172.26 mg, 0.56 mmol) was taken up in dry DMF under argon and sodium azide (182.00 mg, 2.80 mmol) was added. The reaction was then heated to 60° C. for 48 h. The reaction was poured into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with sat NaHCO3 and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (3:1 hexane-ethyl acetate) Yield 122.00 mg. C11H22N2O3 MS m/e=257.3 (M+H).

후처리

  1. extractionthe aqueous layer was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with sat NaHCO3 and brine
  3. dry with materialthen dried over MgSO4
  4. filtrationThe solution was filtered
  5. customthe solvent removed under reduced pressure
  6. customThe product was isolated by flash chromatography

출처 및 근거

ORD 기록
ord-d5a3bc4ce2c14225bbf9dd2e2c11e5bf
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06906067B2

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