Lithium hydroxide, monohydrate → HCID 86727109, compound

HRID 2175924Notes

Reaction equation

HRID 2175924 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]3[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=[O:16])[C:9]3=[N:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1.O[Li:21].O>C1COCC1.CO.O.O>[N:1]1([C:6]2[CH:7]=[C:8]3[CH2:14][CH2:13][CH:12]([C:15]([O-:17])=[O:16])[C:9]3=[N:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1.[Li+:21]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86727108HCID 86727108, compound

Product 1

HCID 86727109HCID 86727109, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a mixture of ethyl 3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate (1.5 g, 5.8 mmol) in 50 mL of THF/MeOH/H2O (2:2:1) was added LiOH.H2O (242.8 mg, 5.8 mmol) portionwise. The resulting mixture was stirred for 30 minutes then diluted with 200 mL of water and washed with ether (3×30 mL). The water layer was freeze-dried to afford the title compound: 1H-NMR (400 MHz, D2O) δ ppm 8.68 (s, 1H), 8.07 (s, 1H), 3.97 (t, J=7.6 Hz, 1H), 3.00-3.14 (m, 2H), 2.53-2.59 (m, 1H), 2.17-2.32 (m, 1H).

Workup

  1. washwashed with ether (3×30 mL)
  2. dry with materialThe water layer was freeze-dried

Sources & evidence

ORD record
ord-08cf39035eb848df97640013e1325623
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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