Water → HCID 67277826, compound

HRID 1695704Notes

Reaction equation

HRID 1695704 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH:14]([CH2:16][O:17][CH3:18])[NH:13][CH:12]([CH2:19][O:20][CH3:21])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:23]([BH3-])#N.[Na+]>C(#N)C.C=O.C(O)(=O)C>[C:1]1([S:7]([N:10]2[CH2:15][CH:14]([CH2:16][O:17][CH3:18])[N:13]([CH3:23])[CH:12]([CH2:19][O:20][CH3:21])[CH2:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 67212627HCID 67212627, compound

Product 1

HCID 67277826HCID 67277826, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 712FormaldehydeSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of the above described (3SR,5SR)-1-benzenesulfonyl-3,5-bis-methoxymethyl-piperazine (1.68 g, 5.343 mmol) in acetonitrile (40 ml) and 36.5% formaldehyde solution in water (0.653 ml, 8.015 mmol) and 5-7 drops of acetic acid at 23° C. was added sodium cyanoborohydride (1.679 g, 26.71 mmol) and the mixture was stirred at 23° C. for 1.5 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 the title compound as a colorless oil (1.05 g, 60%), pure enough for further steps; MS (ISP) m/e=329.1 [(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-c7ca308a66ea4f87be67f664b80ec7b6
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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