Acetic Acid → HCID 118939116, compound

HRID 524002Notes

Reaction equation

HRID 524002 reaction equation
[ClH:1].[F:2][C:3]1([F:18])[CH2:5][CH:4]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH2:14][NH:13][CH2:12][CH2:11]2.C(OC(=O)[NH:25][C@H:26]([C:28]1[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=1)[CH3:27])(C)(C)C.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[ClH:1].[F:18][C:3]1([F:2])[CH2:5][CH:4]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([CH2:34][C:31]1[CH:32]=[CH:33][C:28]([C@@H:26]([NH2:25])[CH3:27])=[CH:29][CH:30]=1)[CH2:12][CH2:11]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 89479126HCID 89479126, compoundHCID 118939072HCID 118939072, compound

Product 1

HCID 118939116HCID 118939116, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 800 mg (2.94 mmol) 6-(2,2-difluoro-cyclopropylmethoxy)-1,2,3,4-tetrahydro-isoquinoline hydrochloride (example XXXII.2) and 806 mg (3.23 mmol) [(S)-1-(4-formyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (example II) in 8 mL THF are added 504 μL (8.81 mmol) AcOH and the mixture is stirred at r.t. for 10 min. After that time, the resulting mixture is cooled to 0° C. and 934 mg (4.41 mmol) sodium triacetoxyborohydride are added and the reaction mixture is stirred at r.t. for 2 h. After that time, the reaction is quenched by addition of 500 μl water, the solvent is removed and and the residue is purified by HPLC.

Workup

  1. temperatureAfter that time, the resulting mixture is cooled to 0° C.
  2. stirringthe reaction mixture is stirred at r.t. for 2 h
  3. customAfter that time, the reaction is quenched by addition of 500 μl water
  4. customthe solvent is removed
  5. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-e70537a6c210431894031284fe834de1
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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