Carbonic acid, bis(1,1-dimethylethyl) ester → HCID 86657788, compound

HRID 401924Notes

Reaction equation

HRID 401924 reaction equation
Cl.Cl.[CH2:3]([C:7]1[N:12]=[N:11][C:10]([O:13][CH2:14][C@H:15]2[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]2[OH:21])=[CH:9][C:8]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:24][CH:23]=1)[CH2:4][CH2:5][CH3:6].[C:35](=O)([O:41]C(C)(C)C)[O:36][C:37]([CH3:40])([CH3:39])[CH3:38]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:37]([O:36][C:35]([N:18]1[CH2:19][CH2:20][C@H:15]([CH2:14][O:13][C:10]2[N:11]=[N:12][C:7]([CH2:3][CH2:4][CH2:5][CH3:6])=[C:8]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:24][CH:23]=3)[CH:9]=2)[C@H:16]([OH:21])[CH2:17]1)=[O:41])([CH3:40])([CH3:39])[CH3:38]

Participants

5

Reactant 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 86657781HCID 86657781, compound

Product 1

HCID 86657788HCID 86657788, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (±)-cis-4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxymethyl]-piperidin-3-ol dihydrochloride (1.14 mmol, 0.50 g) in DCM and saturated NaHCO3 (1 M, 1:1, v/v), was added di-t-butyl carbonate (3.42 mmol, 0.75 g). The reaction was stirred for 1 hour at room temperature. The reaction was allowed to settle and the layers were separated. The organic layer was dried and the crude product was purified by flash chromatography to give (±)-cis-4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxymethyl]-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.50 g).

Workup

  1. customthe layers were separated
  2. customThe organic layer was dried
  3. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ee37658ac13c4670a5a27d8437e8ddfd
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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