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

HRID 1257572Notes

Reaction equation

HRID 1257572 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d8e97f214799432a824e2fad5098317c
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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