Dimethylamine → Tert-butyl{4-[(dimethylamino)carbonyl]cyclohexyl}carbamate

HRID 449356Notes

Reaction equation

HRID 449356 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)C.[C:8]([O:12][C:13]([NH:15][CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=O)[CH2:18][CH2:17]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].CNC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.O>[C:8]([O:12][C:13](=[O:14])[NH:15][CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([N:3]([CH3:4])[CH3:1])=[O:24])[CH2:18][CH2:17]1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27559964-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

Product 1

HCID 69309396Tert-butyl{4-[(dimethylamino)carbonyl]cyclohexyl}carbamateYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.42 mL, 3.0 mmol) was added to a mixture of 4-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid (1.0 mmol), dimethylamine (0.6 mL, 1.2 mmol) (2 N THF solution) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.46 g, 1.1 mmol) in methylene chloride (5.0 mL). The mixture was stirred at r.t. overnight. The mixture was diluted with water, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-40%) to afford the desired product (0.20 g, 74%). Analytic LCMS (M+Na)+: m/z=293.1; (M-Boc+H)+: m/z=171.1.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-40%)

Sources & evidence

ORD record
ord-6f3d07bd2d67449cbdcd40d6b1dcb2b9
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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