4-tert-Butylcyclohexylamine → HCID 178445668, compound

HRID 1717698Notes

Reaction equation

HRID 1717698 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[C:12]([CH:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13].[BH4-].[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:17][CH2:18]1)[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 793964-tert-ButylcyclohexylamineHCID 5206955-Bromo-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 178445668HCID 178445668, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-1-indanone (6.33 g, 30.0 mmol), titanium (IV) isopropoxide (17.8 mL, 60.0 mmol), 4-tert-butylcyclohexyl amine (9.32 g, 60.0 mmol) in absolute ethanol (200 mL) was stirred under nitrogen at room temperature for 8 h. Sodium borohydride (1.70 g, 45.0 mmol) was then added and the resulting mixture was stirred for an additional 18 h at room temperature. The reaction was quenched by pouring into aqueous ammonia (2N, 300 mL). The resulting inorganic precipitate was filtered off through Celite and washed with CH2Cl2 (300 mL). The organic layer was separated and the remaining aqueous layer was extracted once with CH2Cl2 (100 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. Chromatography (10% to 20% EtOAc in Hexane) afforded (5-bromo-2,3-dihydro-1H-inden-1-yl)(trans-4-tert-butylcyclohexyl). HPLC/MS: m/z=350.1, (M+1), Rt=3.01 min. 1H NMR (CDCl3): δ 7.38 (1H, br s), 7.34 (1H, d, J=8.0 Hz), 7.24 (1H, d, J=8.0 Hz), 4.32 (1H, t, J=6.5 Hz), 3.00 (1H, ddd, J=5.0 Hz, 8.0 Hz, 16.0 Hz), 2.81 (1H, dt, J=8.0 Hz, 16.0 Hz), 2.61 (1H, m), 2.46 (1H, m), 2.08 (1H, m), 2.00 (1H, m), 1.86-1.78 (4H, m), 1.20-1.04 (4H, m), 0.90 (9H, s).

Workup

  1. stirringthe resulting mixture was stirred for an additional 18 h at room temperature
  2. customThe reaction was quenched
  3. additionby pouring into aqueous ammonia (2N, 300 mL)
  4. filtrationThe resulting inorganic precipitate was filtered off through Celite
  5. washwashed with CH2Cl2 (300 mL)
  6. customThe organic layer was separated
  7. extractionthe remaining aqueous layer was extracted once with CH2Cl2 (100 mL)
  8. dry with materialThe combined organic extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customChromatography (10% to 20% EtOAc in Hexane) afforded (5-bromo-2,3-dihydro-1H-inden-1-yl)(trans-4-tert-butylcyclohexyl)

Sources & evidence

ORD record
ord-17ffc5cac0ad4724927e0d52146e2565
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

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