Ammonium formate → HCID 11003421, compound

HRID 1108484Notes

Reaction equation

HRID 1108484 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][C@@H:22]([CH2:32][Cl:33])[C:12]2=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCCC1.[C].[Pd]>[C:28]([O:27][C:25]([N:24]1[C:11]2[C:12](=[C:13]3[C:17](=[C:9]([OH:8])[CH:10]=2)[NH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14]3)[C@H:22]([CH2:32][Cl:33])[CH2:23]1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86755416HCID 86755416, compound

Product 1

HCID 11003421HCID 11003421, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

150.7 mg (0.32 mmole) of methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-chloromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-7-carboxylate and 90 mg of 10% palladium carbon were suspended in 4 ml of tetrahydrofuran, and 1 ml of 25% ammonium formate aqueous solution was added dropwise under ice-cold condition, followed by stirring for 1 hour. The resulting reaction mixture was extracted with ethyl acetate, the obtained organic layer was dried over anhydrous sodium sulfate, and filtrated, followed by concentration to give a residue. The residue was then purified by silica gel column chromatography using an eluate of hexane:ethyl acetate (1:1), followed by crystallization with hexane to give 115.9 mg of methyl (1S)-3-t-butoxycarbonyl-1-chloromethyl-5-hydroxy-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-7-carboxylate. Yield, 95%. NMR (CDCl3) δ: 1.58 (9H, s), 3.54 (1H, t, J=9.8 Hz), 3.87-3.94 (2H, m), 3.96 (3H, s), 4.06 (1H, m), 4.17 (1H, dd, J=9.3, 11.7 Hz), 6.36 (1H, brs), 7.08 (1H, s), 7.64 (1H, brs), 9.23 (1H, brs). [α]D25 =-42.6° (c 0.21, methanol).

Workup

  1. customThe resulting reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationfollowed by concentration
  6. customto give a residue
  7. customThe residue was then purified by silica gel column chromatography
  8. customfollowed by crystallization with hexane

Sources & evidence

ORD record
ord-f037d3609a724f2eb050922b6d35e4ea
Source dataset
uspto-grants-2000_05
Patent number
US06066742

Reaction notes

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