Tert-Butylamine → HCID 71290297, compound

HRID 1944820Notes

Reaction equation

HRID 1944820 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26].C1COCC1.[Li][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1>CCOCC.O>[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8028TetrahydrofuranHCID 86663391HCID 86663391, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 71290297HCID 71290297, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-80 °C

Procedure

A mixture of 4.10 g (12.9 mmol) of 6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde, 2.83 g (38.7 mmol) of tert-butylamine, 90 g of molecular sieves (4A), and 80 ml of THF was stirred overnight. After decantation of the molecular sieves (they were additionally washed by 2×50 ml of THF), the resulting combined solution was additionally centrifuged to remove slight precipitate. The obtained solution was evaporated to dryness. A solution of the residue in 80 ml of THF was cooled to −80° C., and 50.0 ml (37.5 mmol) of 0.75 M of PhLi in ether was added. The resulting mixture was stirred for 1 h at room temperature. Further on, 20 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 2×40 ml of ether. The combined organic extract was washed by 20 ml of water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; ethyl acetate-triethylamine=20:1, vol.). Yield 2.84 g (49%) of white solid of a ca. 1 to 1 mixture of two diastereomers. Anal. calc. for C31H37N3: C, 82.44; H, 8.26; N, 9.30. Found: C, 82.59; H, 8.35; N, 9.19. For 1H NMR (in CDCl3) see FIG. 2—Top spectrum.

Workup

  1. washAfter decantation of the molecular sieves (they were additionally washed by 2×50 ml of THF), the resulting
  2. customto remove slight precipitate
  3. customThe obtained solution was evaporated to dryness
  4. stirringThe resulting mixture was stirred for 1 h at room temperature
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with 2×40 ml of ether
  7. extractionThe combined organic extract
  8. washwas washed by 20 ml of water
  9. dry with materialdried over K2CO3
  10. customevaporated to dryness
  11. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; ethyl acetate-triethylamine=20:1, vol.)

Sources & evidence

ORD record
ord-2e23b904ffe84e5b900dbf52420e2684
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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