Triethylamine → benzyl((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)carbamate

HRID 1592337Notes

Reaction equation

HRID 1592337 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH2:13])[CH2:7][CH2:6]2.[CH:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[CH2:25]([O:24][C:23](=[O:32])[NH:22][C@@H:17]1[CH2:18][CH2:19][CH2:20][CH2:21][C@H:16]1[CH2:14][NH:13][CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([F:2])[CH:4]=2)[CH2:9]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 196993636-Fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochlorideHCID 29923903Benzyl [(1r,2r)-2-formylcyclohexyl]carbamate

Product 1

HCID 131726668benzyl((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)carbamateYield 69%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of (RS)-(6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amine hydrochloride (200 mg, 0.99 mmol) and benzyl [(1R,2R)-2-formylcyclohexyl]carbamate (258 mg, 0.99 mmol) in 1,2-dichloroethane (4 mL) was treated with triethylamine (275 μL, 1.98 mmol) whereupon a clear solution resulted. Sodium triacetoxyborohydride (272 mg, 1.28 mmol) was added and the mixture was stirred at room temperature for 3.5 hours. Aqueous sodium hydroxide (1.0 N) was then added, and the mixture was extracted with ether. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography, eluting with 5% methanol in dichloromethane, containing 0.5% aqueous ammonia, to provide a colorless oil (280 mg, 69%).

Workup

  1. customresulted
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography
  6. washeluting with 5% methanol in dichloromethane
  7. additioncontaining 0.5% aqueous ammonia

Sources & evidence

ORD record
ord-4ad87b87e83a4e578a618c6ed8b3d526
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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