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

HRID 1257572ノート

反応式

HRID 1257572 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d8e97f214799432a824e2fad5098317c
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

反応ノート

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