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

HRID 1722270
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HRID 1722270 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-039dd923b5b949f596afb454a72b2464
출처 데이터셋
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04855286

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