Formic Acid → HCID 86716575, compound

HRID 715489Notes

Reaction equation

HRID 715489 reaction equation
[CH3:1][C@:2]1([CH2:24][NH:25][C:26]2[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=2[N+:34]([O-])=O)[C:29]#[N:30])[CH2:23][CH2:22][CH2:21][C:4]2([O:8][C@H:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C@@H:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:5]2)[CH2:3]1.CO.[CH:39](OC)(OC)OC.C(O)=O>[Fe].CCOC(C)=O>[CH3:1][C@:2]1([CH2:24][N:25]2[C:26]3[CH:27]=[C:28]([C:29]#[N:30])[CH:31]=[CH:32][C:33]=3[N:34]=[CH:39]2)[CH2:23][CH2:22][CH2:21][C:4]2([O:8][C@H:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C@@H:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:5]2)[CH2:3]1

Participants

7

Reactant 4

HCID 284Formic Acid2×HCID 887MethanolHCID 9005Trimethyl orthoformate2×HCID 71116075HCID 71116075, compound

Product 1

HCID 86716575HCID 86716575, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
64 °C

Procedure

A 5 L three neck flask was fitted with a mechanical stirrer and condenser. To the flask was added 3-({[(2R,3R,7S)-7-methyl-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-7-yl]methyl}amino)-4-nitrobenzonitrile (245.5 g, 508 mmol), MeOH (891 mL) and EtOAc (891 mL). Next, trimethyl orthoformate (561 mL, 5077 mmol) and formic acid (195 mL, 5077 mmol) were added. The resulting mixture was heated at 64° C. Next, (2-3 eq) of formic acid, trimethylorthoformate and iron were added every 15 min until the reaction was finished (3.5 h). Next, the mixture was filtered to remove excess iron, and the iron was washed with EtOAc. The filtrate was concentrated and the resulting thick purple residue (residue contained formic acid) was used without further purification (235 g, 100% yield).

Workup

  1. custom(3.5 h)
  2. filtrationNext, the mixture was filtered
  3. customto remove excess iron
  4. washthe iron was washed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. customthe resulting thick purple residue (residue contained formic acid) was used without further purification (235 g, 100% yield)

Sources & evidence

ORD record
ord-b8c27faccdae4f809ed1125313fa89a9
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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