Benzophenone imine → (1R,2R)-2-(diphenylmethyleneamino)cyclopentanol

HRID 238753Notes

Reaction equation

HRID 238753 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[OH:14].[C:15]1([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[C:15]1([C:21](=[N:8][C@@H:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[OH:14])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 86612967(1R,2R)-2-Amino-cyclopentanol Trifluoroacetic Acid Salt

Product 1

HCID 59458819(1R,2R)-2-(diphenylmethyleneamino)cyclopentanolYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2R)-2-aminocyclopentanol TFA salt (630 mg, 2.93 mmol) was added diphenylmethanimine (490 uL, 2.93 mmol) and TEA (0.5 mL, 3.58 mmol) in CH2Cl2 (3 mL). The reaction mixture was stirred at rt for 2 h and concentrated under reduced pressure and purified by ISCO flash chromatography using EtOAc and hexane as eluting solvent to yield (1R,2R)-2-(diphenylmethyleneamino)cyclopentanol (697 mg, 90% yield) as a colorless gum. HPLC: RT=1.96 min [M+H] 266.13 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm); 1H NMR (400 MHz, CDCl3) δ ppm 1.49-1.64 (m, 2H), 1.66-1.91 (m, 3H), 2.08-2.24 (m, 1H), 3.55-3.71 (m, 1H), 4.31-4.47 (m, 1H), 7.15-7.25 (m, 2H), 7.29-7.53 (m, 6H), 7.61-7.67 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by ISCO flash chromatography
  3. washas eluting solvent

Sources & evidence

ORD record
ord-46be580af168466ea91e222a15205d42
Source dataset
uspto-grants-2014_02
Patent number
US08642576B2

Reaction notes

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