Diethyl Ether → (R)-tetrahydrofuran-2-ylmethyl-cyanamide

HRID 1931079Notes

Reaction equation

HRID 1931079 reaction equation
[N:1]#[C:2]Br.C([O-])([O-])=O.[Na+].[Na+].[CH3:10][NH2:11].[CH3:12][CH2:13][O:14][CH2:15][CH3:16]>>[O:14]1[CH2:15][CH2:16][CH2:12][C@@H:13]1[CH2:10][NH:11][C:2]#[N:1]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6329MethylamineHCID 10340Sodium CarbonateHCID 10476Cyanogen Bromide

Product 1

HCID 55288151(R)-tetrahydrofuran-2-ylmethyl-cyanamide

Procedure

To a stirred mixture of cyanogen bromide (2.2 g, 20.8 mmol) and anhydrous Na2CO3 (4.2 g, 39.6 mmol) in dry ether (30 mL) cooled between −20 and −10° C. was added (R)-tetrahydro-furan-2-yl)-methylamine (Aldrich) (2.0 g, 19.8 mmol) over 10 minutes. Stirring was continued for an additional 1.5 hours at −20 to −10° C. Then the mixture was filtered and concentrated to provide 2.21 g of the title product. MS (ESI) m/z 127 (M+H)+.

Workup

  1. temperaturecooled between −20 and −10° C.
  2. filtrationThen the mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d7dfa2d5949946cbabe4ce12ee444c37
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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