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Water → 2-(S)-(2-Cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20369
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HRID 20369 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][OH:15])[CH2:12][O:11][C@@H:10]([CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.O>CS(C)=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH:14]=[O:15])[CH2:12][O:11][C@@H:10]([CH2:16][CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 3

HCID 962WaterHCID 8471TriethylamineHCID 685596732-(S)-(2-Cyclohexylethyl)-5-(S)-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

생성물 1

HCID 866153612-(S)-(2-Cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 8857
Ethyl Acetate
용매

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온도
10 °C

실험 절차

Dissolve 2-(S)-(2-cyclohexylethyl)-5-(S)-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester (165 mg, 0.50 mmol) in dimethylsulfoxide (2 mL), and cool to 10° C. Add triethylamine (0.28 mL, 2.02 mmol) followed by pyridine sulfur trioxide complex and stir for 30 min. Dilute with ethyl acetate and pour into cold water. Wash with 5% citric acid (50 mL), saturated aqueous sodium chloride (50 mL) and dry (sodium sulfate), filter and concentrate give the desired compound as an oil which is used without further purification.

후처리

  1. washWash with 5% citric acid (50 mL), saturated aqueous sodium chloride (50 mL)
  2. dry with materialdry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate

출처 및 근거

ORD 기록
ord-2ba6262a95b94b529d2492702735d006
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745438B2

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