Ethyl Acetate → 1,5-bis(t-butoxycarbonyl)-2-hydroxymethyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 352870Notes

Reaction equation

HRID 352870 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C:11]=2[CH:10]=[C:9]1[CH2:24][O:25][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F.C(OCC)(=O)C>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C:11]=2[CH:10]=[C:9]1[CH2:24][OH:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14917Hydrofluoric AcidHCID 113307771,5-Bis(t-butoxycarbonyl)-2-(t-butyldiphenylsiloxy)methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 113487371,5-bis(t-butoxycarbonyl)-2-hydroxymethyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 1,5-bis(t-butoxycarbonyl)-2-(t-butyldiphenylsiloxy)methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (2.10 g) in pyridine (20 ml), a mixture of hydrogen fluoride and pyridine was added at 0° C., followed by stirring at room temperature for 1 hour. After the reaction mixture was poured into ethyl acetate (50 ml) and ice water (300 ml) which had been stirred in advance, the resulting mixture was separated. The water layer was extracted with ethyl acetate (50 ml). The organic layers were combined, washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column (150 g of silica gel, hexane:ethyl acetate=3:1), whereby the title compound (882 mg) was obtained as a colorless, transparent caramel-like substance.

Workup

  1. additionwas added at 0° C.
  2. stirringhad been stirred in advance
  3. customthe resulting mixture was separated
  4. extractionThe water layer was extracted with ethyl acetate (50 ml)
  5. washwashed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by chromatography on a silica gel column (150 g of silica gel, hexane:ethyl acetate=3:1), whereby the title compound (882 mg)
  10. customwas obtained as a colorless, transparent caramel-like substance

Sources & evidence

ORD record
ord-c2f5698c7ab840e2af66102b03351afb
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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