Pyridine → HCID 58635315, compound

HRID 1012867Notes

Reaction equation

HRID 1012867 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-bdbd11b0e88f4b809341474433011d76
Source dataset
uspto-grants-2011_07
Patent number
USRE042562E1

Reaction notes

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