Triphenylphosphine → (S)-tert-butyl tetrahydro-2H-pyran-3-ylcarbamate

HRID 1257572노트

반응식

HRID 1257572 반응식
O[CH2:2][C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:5][CH2:6][OH:7].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[O:7]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:2]1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 2734851tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidateHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 67324694(S)-tert-butyl tetrahydro-2H-pyran-3-ylcarbamate수율 63.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A 20-L reactor equipped with a mechanical stirrer was charged with (S)-tert-butyl 1,5-dihydroxypentan-2-ylcarbamate (950 g, 4.33 mol), Ph3P (2272 g, 8.66 mol) and DCM (10 L). Then DIAD (1751 g, 8.66 mol) was added dropwise to the reaction solution. The solution was stirred for 48 h at room temperature until the reaction was complete. After filtration and concentration in vacuo, the residue was purified by column chromatography with petroleum ether as eluent to give 550 g of (S)-tert-butyl tetrahydro-2H-pyran-3-ylcarbamate as white solid. 1H NMR (400 MHz, CDCl3) δ 4.77 (m, 1H), 3.78 (d, J=11.1 Hz, 1H), 3.63 (d, J=8.8 Hz, 3H), 3.38 (m, 1H), 1.88 (td, J=8.4, 3.8 Hz, 1H), 1.74 (ddd, J=10.4, 9.1, 4.9 Hz, 1H), 1.65-1.51 (m, 2H), 1.45 (s, 9H).

후처리

  1. customA 20-L reactor equipped with a mechanical stirrer
  2. filtrationAfter filtration and concentration in vacuo
  3. customthe residue was purified by column chromatography with petroleum ether as eluent

출처 및 근거

ORD 기록
ord-d8e97f214799432a824e2fad5098317c
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461328B2

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