Sodium hydride → benzyl[(2S)-1,4-dioxan-2-ylmethyl]methylcarbamate

HRID 1987105Notes

Reaction equation

HRID 1987105 reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CS(O[CH2:20][C@H:21]1[CH2:26][O:25][CH2:24][CH2:23][O:22]1)(=O)=O>CN(C)C=O.C(OCC)C>[O:22]1[CH2:23][CH2:24][O:25][CH2:26][C@@H:21]1[CH2:20][N:4]([CH3:3])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 562265benzyl N-methylcarbamateHCID 86609782(2R)-1,4-dioxan-2-ylmethyl methanesulfonate

Product 1

HCID 53309827benzyl[(2S)-1,4-dioxan-2-ylmethyl]methylcarbamate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (29 mg, 0.74 mmol) was suspended in 2 mL of N,N-dimethylformamide (DMF) and cooled to 0° C. A solution of benzyl methylcarbamate (81 mg, 0.49 mmol) in 2 mL of DMF was added via syringe. After 20 minutes, a solution of (2R)-1,4-dioxan-2-ylmethyl methanesulfonate (191 mg, 0.97 mmol) in 2 mL of DMF was added by syringe and the mixture was heated to 70° C. After 2 h the mixture was cooled to ambient temperature, then diluted in diethyl ether, washed with water and brine, then dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (silica, ethylacetate/hexanes) to afford the title compound. LRMS (APCI) calc'd for (C14H20NO4) [M+H]+, 266.1; found, 266.2.

Workup

  1. temperaturethe mixture was heated to 70° C
  2. temperatureAfter 2 h the mixture was cooled to ambient temperature
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica, ethylacetate/hexanes)

Sources & evidence

ORD record
ord-37c6f5b4383947e5af89f5e73fe68d74
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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