Water → HCID 67212526, compound

HRID 1695708Notes

Reaction equation

HRID 1695708 reaction equation
[C:1]1([S:7]([N:10]2[CH2:17][CH:16]3[NH:18][CH:12]([CH2:13][O:14][CH2:15]3)[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:20]([BH3-])#N.[Na+]>C(#N)C.C=O.C(O)(=O)C>[NH3:10].[C:1]1([S:7]([N:10]2[CH2:11][CH:12]3[N:18]([CH3:20])[CH:16]([CH2:15][O:14][CH2:13]3)[CH2:17]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 67212430HCID 67212430, compound

Product 2

HCID 222AmmoniaHCID 67212526HCID 67212526, compoundYield 133.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 712FormaldehydeSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of the above described 7-benzenesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane (1.25 g, 4.658 mmol) in acetonitrile (40 ml) and 36.5% formaldehyde solution in water (0.53 ml, 6.987 mmol) and 5 drops of acetic acid at 23° C. was added sodium cyanoborohydride (1.464 g, 23.29 mmol) and the mixture was stirred at 23° C. for 2 h. Poured onto water and extracted twice with ethyl acetate, dried the organic layer over sodium sulfate, filtered off, evaporated all volatiles totally and dried in high vacuum to give after silica gel column chromatography with ethyl acetate and additional methanol and aqueous ammonia solution the title compound as a colorless oil (0.88 g, 67%), MS (ISP) m/e=283.1 [(M+H)+].

Workup

  1. additionTo a mixture of the
  2. additionPoured onto water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialdried the organic layer over sodium sulfate
  5. filtrationfiltered off
  6. customevaporated all volatiles totally
  7. customdried in high vacuum

Sources & evidence

ORD record
ord-51a9defc6b4140ebbd75bd3f1e939bd5
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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