Hydrochloric Acid → HCID 89754182, compound

HRID 2173427Notes

Reaction equation

HRID 2173427 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=O)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1.Cl.[OH-].[Na+]>C1COCC1>[N:1]1([C:6]2[CH:7]=[C:8]([CH2:12][CH2:13][N:15]3[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]3)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86693040HCID 86693040, compound

Product 1

HCID 89754182HCID 89754182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-{[3-(1H-tetrazol-1yl)phenyl]acetyl}piperazine-1-carboxylate (0.80 g, 2.148 mmol) was dissolved in THF (20 ml) and added the borane-tetrahydrofuran complex (4.30 ml, 4.30 mmol) then stirred at RT overnight. TLC showed a less polar spot but still has SM. Added another 2 equiv of borane-THF complex and followed the reaction with TLC. The reaction was first shaken with 1N HCl then basified with 1N NaOH and extracted with ETOAc. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed by MPLC-using 40 g ISCO Redi-sep column and eluted with 50% ethyl acetate/50% hexane to yield t-butyl 4-{2-[3-(1H-tetrazol-1yl)phenyl]ethyl}piperazine-1-carboxylate. LC-MS (IE, m/z): 359 [M+1]+; 1H-NMR (500 MHz, CDCl3) δ ppm 9.04 (s, 1H), 7.64 (s, 1H), 7.60 (t, J=8.2 Hz, 1H), 7.57 (t, J=7.9 Hz, 1H), 7.44 (d, J=7.3 Hz, 1H), 3.87 (b, 4H), 3.32-3.36 (m, 2H), 3.12 (d, J=11.9 Hz, 2H), 3.024-3.06 (m, 2H), 2.70-2.75 (m, 2H), 1.49 (s, 9H);

Workup

  1. additionadded the borane-tetrahydrofuran complex (4.30 ml, 4.30 mmol)
  2. additionAdded another 2 equiv of borane-THF complex
  3. customthe reaction with TLC
  4. extractionextracted with ETOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was chromatographed by MPLC-using 40 g ISCO Redi-sep column
  9. washeluted with 50% ethyl acetate/50% hexane

Sources & evidence

ORD record
ord-a38b2e97587e4c9280e8533ddcd8b447
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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