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Triphenylphosphine → 3-Boc-4(S)-Cyclohexylmethyl-2,2-dimethyl-5-(2-bromoethyl)oxazolidine

HRID 1722270
ノート
印刷プレビュー

反応式

HRID 1722270 の反応式
N(C(OCC)=O)=NC(OCC)=O.[C:13]([N:20]1[C@@H:24]([CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:23]([CH2:32][CH2:33]O)[O:22][C:21]1([CH3:36])[CH3:35])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br-:56].[NH+]1C=CC=CC=1>C(Cl)Cl.O>[C:13]([N:20]1[C@@H:24]([CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:23]([CH2:32][CH2:33][Br:56])[O:22][C:21]1([CH3:36])[CH3:35])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11309665Pyridinium bromideHCID 186342693-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5-(2-hydroxyethyl)oxazolidine

生成物 1

HCID 186342683-Boc-4(S)-Cyclohexylmethyl-2,2-dimethyl-5-(2-bromoethyl)oxazolidine

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

1.6 ml of diethyl azodicarboxylate are added dropwise, at 20° C. under argon, to 690 mg of 3-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5-(2-hydroxyethyl)oxazolidine, 2.6 g of triphenylphosphine and 1.6 g of pyridinium bromide in 15 ml of CH2Cl2. After 16 h at R.T., H2O is added and the mixture is diluted with 100 ml of CH2Cl2. The organic phase is washed twice with saturated NaHCO3 solution and once with saturated NaCl solution. The organic phase is dried with Na2SO4 and concentrated, and the residue is taken up in a little EA and filtered to remove PPh3. Purification on silica gel provides the title compound (eluent: H/EA 15:1).

後処理

  1. washThe organic phase is washed twice with saturated NaHCO3 solution and once with saturated NaCl solution
  2. dry with materialThe organic phase is dried with Na2SO4
  3. concentrationconcentrated
  4. filtrationfiltered
  5. customto remove PPh3
  6. customPurification on silica gel

出典と根拠

ORDレコード
ord-039dd923b5b949f596afb454a72b2464
出典データセット
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04855286

反応ノート

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