Ethanol → HCID 59772980, compound

HRID 2220154Notes

Reaction equation

HRID 2220154 reaction equation
FC(F)(F)S(C1C=C(C=CC=1)N[CH:10]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:12][CH2:11]1)(=O)=O.[OH-:32].[NH4+].[CH2:34]([OH:36])[CH3:35]>>[O:36]1[C:10]2([CH2:11][CH2:12][N:13]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([CH2:23][NH2:24])=[CH:25][CH:26]=3)(=[O:17])=[O:18])[CH2:14][CH2:15]2)[O:32][CH2:35][CH2:34]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 67353620HCID 67353620, compound

Product 1

HCID 59772980HCID 59772980, compoundYield 90%

Procedure

The catalyst (Aldrich Palladium, 5 wt % (dry basis) on activated carbon as 50 wt % suspension in water (Degussa type E101 NO/W), 3.0 g, 0.70 mmol) was charged to a flask, which was evacuated and purged with nitrogen three times. A solution of nitrile 1a (14.0 g, 45.4 mmol) in ethanol (450 ml) and concentrated aqueous ammonium hydroxide solution (31 wt %, 40 ml, 620 mmol) were added. The flask was evacuated and purged with nitrogen three times then evacuated and filled with hydrogen twice. The reaction was stirred at room temp under hydrogen at balloon pressure and monitored by TLC (5% methanol in DCM) until complete (1-2 days). When complete, the flask was evacuated and purged with nitrogen three times, the catalyst was filtered off through a glass fibre filter paper and washed with hot ethanol (3×100 ml). The reaction was worked up as follows: the filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (25 fold weight of silica based on crude product) using a gradient elution with 5-50% methanol in DCM which yielded 90% of [4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylsulfonyl)phenyl]methanamine 7b.

Workup

  1. dry with materialThe catalyst (Aldrich Palladium, 5 wt % (dry basis) on activated carbon as 50 wt % suspension in water (Degussa type E101 NO/W), 3.0 g, 0.70 mmol)
  2. additionwas charged to a flask
  3. customwhich was evacuated
  4. custompurged with nitrogen three times
  5. customThe flask was evacuated
  6. custompurged with nitrogen three times
  7. customthen evacuated
  8. additionfilled with hydrogen twice
  9. custommonitored by TLC (5% methanol in DCM) until complete (1-2 days)
  10. customWhen complete, the flask was evacuated
  11. custompurged with nitrogen three times
  12. filtrationthe catalyst was filtered off through a glass fibre
  13. filtrationfilter paper
  14. washwashed with hot ethanol (3×100 ml)
  15. customthe filtrate was evaporated to dryness
  16. customthe residue was purified by column chromatography on silica gel (25 fold weight of silica based on crude product)
  17. washa gradient elution with 5-50% methanol in DCM which

Sources & evidence

ORD record
ord-821baa0447984163b36d6a86104d478d
Source dataset
uspto-grants-2008_08
Patent number
US07417058B2

Reaction notes

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