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

HRID 339481

反応式

HRID 339481 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-1566ce787f12493aade5926d04773a8c
出典データセット
uspto-grants-2014_11
特許番号
US08895497B2

関連ノート

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