Pyridine → HCID 58635315, compound

HRID 1826682Notes

Reaction equation

HRID 1826682 reaction equation
[NH2:1][C@@H:2]([CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[CH2:3][CH2:4][OH:5].N1C=CC=CC=1.[C:21](Cl)(Cl)=[O:22]>C(Cl)Cl>[Si:8]([O:7][CH2:6][C@H:2]1[CH2:3][CH2:4][O:5][C:21](=[O:22])[NH:1]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 58635311HCID 58635311, compound

Product 1

HCID 58635315HCID 58635315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R)-3-amino-4-{[tert-butyl(dimethyl)silyl]oxy}butan-1-ol (2.63 g, 12 mmol) in DCM (100 mL) at 0° C. was added pyridine (3 mL) followed by phosgene (20% solution in toluene, 1.9 M, 8.5 mL) dropwise and the mixture was stirred for 30 min and allowed to warm to rt, and quenched with water. The layers were separated and the water layer extracted with DCM once. The organic layers were dried over MgSO4, filtered and concentrated. The desired product (4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-oxazinan-2-one was obtained from crystallization from ether/hexanes at −20° C. as a light yellow solid. 1H NMR (400 MHz, CDCl3) 5.52 (br s, 1H), 4.38–4.33 (m, 1H), 4.28–4.22 (m, 1H), 3.70–3.59 (m, 2H), 3.46 (t, 1H), 1.97–1.93 (m, 1H), 1.72–1.67 (m, 1H), 0.91 (s, 9H), 0.90 (s, 6H).

Workup

  1. customquenched with water
  2. customThe layers were separated
  3. extractionthe water layer extracted with DCM once
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f185a6eee13c4e65b6f8b8f032c3af14
Source dataset
uspto-grants-2006_05
Patent number
US07053085B2

Reaction notes

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