Acetic Acid → HCID 118939107, compound

HRID 524015Notes

Reaction equation

HRID 524015 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[CH2:12][NH:11][CH2:10][CH:9]3[F:16])[CH2:3][CH2:2]1.C(OC(=O)[NH:23][C@H:24]([C:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1)[CH3:25])(C)(C)C.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[CH2:12][N:11]([CH2:32][C:29]2[CH:30]=[CH:31][C:26]([C@@H:24]([NH2:23])[CH3:25])=[CH:27][CH:28]=2)[CH2:10][CH:9]3[F:16])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 89479126HCID 89479126, compoundHCID 118939137HCID 118939137, compound

Product 1

HCID 118939107HCID 118939107, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 170 mg (0.660 mmol) 6-cyclopropylmethoxy-4-fluoro-1,2,3,4-tetrahydro-isoquinoline (example XLVII.5) and 164 mg (0.660 mmol) [(S)-1-(4-formyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (example II) in 2 mL THF are added 113 μL (1.98 mmol) AcOH and the mixture is stirred at r.t. for 10 min. The resulting mixture is cooled to 0° C., 210 mg (0.989 mmol) sodium triacetoxyborohydride are added and the reaction mixture is stirred at r.t. for 2 h. The reaction is quenched by the addition of 200 μL water and purified by HPLC (ACN/H2O/NH3).

Workup

  1. temperatureThe resulting mixture is cooled to 0° C.
  2. stirringthe reaction mixture is stirred at r.t. for 2 h
  3. customThe reaction is quenched by the addition of 200 μL water
  4. custompurified by HPLC (ACN/H2O/NH3)

Sources & evidence

ORD record
ord-38da0af780e2496892200af901e4d40a
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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