Benzhydrylamine → HCID 178420361, compound

HRID 1844423Notes

Reaction equation

HRID 1844423 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]1([CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:20]([NH:21][C@H:10]1[CH2:11][CH2:12][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:20]([NH:21][C@H:10]1[CH2:11][CH2:12][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7036BenzhydrylamineHCID 786054-PhenylcyclohexanoneHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 178420361HCID 178420361, compoundYield 74.9%HCID 178420362HCID 178420362, compoundYield 19.49%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-phenylcyclohexanone (500 mg, 2.87 mmol) and diphenylmethanamine (526 mg, 2.87 mmol) in DCE (4 mL) at 0° C. was added sodium triacetoxyborohydride (912 mg, 4.30 mmol) by portions slowly. A white suspension resulted and was stirred for 5 min before the ice-water bath was removed. The reaction was stirred at rt for 1.5 h. The reaction was quenched with water carefully, then saturated NaHCO3 was added carefully and the aqueous was extracted with DCM (3×). The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated. The residue was purified by ISCO flash chromatography (0-100% hexane/EtOAc) to give Intermediate 30A (734 mg, 2.149 mmol, 74.9% yield) and trans-N-benzhydryl-4-phenylcyclohexanamine (191 mg, 0.559 mmol, 19.49% yield), LC-MS (ESI) m/z 342.1 (M+H), RT=1.76 min (Method B). 1H NMR (400 MHz, chloroform-d) δ ppm 7.37 (4 H, d, J=7.33 Hz), 7.23-7.31 (6 H, m), 7.11-7.23 (5 H, m), 4.91 (1 H, s), 2.80-2.88 (1 H, m), 2.46-2.56 (1 H, m), 1.74-1.90 (4 H, m), 1.60-1.70 (2H, m), 1.47-1.59 (2 H, m).

Workup

  1. customA white suspension resulted
  2. customwas removed
  3. customThe reaction was quenched with water carefully
  4. additionsaturated NaHCO3 was added carefully
  5. extractionthe aqueous was extracted with DCM (3×)
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by ISCO flash chromatography (0-100% hexane/EtOAc)

Sources & evidence

ORD record
ord-7b2b99d70fc94c7ab4fb0f9b30d04dfe
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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