Triacetoxyperiodinane → (S)-tert-butyl 3-(benzyloxy)-1-oxopropan-2-ylcarbamate

HRID 339481

반응식

HRID 339481 반응식
[CH2:1]([O:8][CH2:9][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

생성물 1

HCID 11196731(S)-tert-butyl 3-(benzyloxy)-1-oxopropan-2-ylcarbamate수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl N-[(1R)-2-(benzyloxy)-1-(hydroxymethyl)ethyl]carbamate (1.2 g, 4.3 mmole) was dissolved in CH2Cl2 (40 mL). Dess-Martin periodinane (2.4 g, 5.5 mmole) was added. The solution was stirred for 2 h at room temperature and then quenched with Na2S2O3 and saturated bicarbonate solution. After extracting with CH2Cl2, the organic layer was dried over MgSO4, filtered, and concentrated by rotary evaporation. Purification by chromatography (silica, 4/1: Hexane/EtOAc, Rf=0.4) afforded (S)-tert-butyl 1-(benzyloxy)-3-oxopropan-2-ylcarbamate as a white solid (1.1 g, 96%).

후처리

  1. customquenched with Na2S2O3 and saturated bicarbonate solution
  2. extractionAfter extracting with CH2Cl2
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customPurification by chromatography (silica, 4/1: Hexane/EtOAc, Rf=0.4)

출처 및 근거

ORD 기록
ord-1566ce787f12493aade5926d04773a8c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895497B2

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