Di-tert-butyl dicarbonate → HCID 10968084, compound

HRID 2217185Notes

Reaction equation

HRID 2217185 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O>CC#N.CN(C1C=CN=CC=1)C>[C:18]([O:17][C:15]([N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:14])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 1514115HCID 1514115, compound

Product 1

HCID 10968084HCID 10968084, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of (S)-piperidine-2-carboxylic acid tert-butyl ester (M. Egbertson and S. J. Danishefsky, J. Org. Chem., 1989, 54, 1, 11-12) (5.78 g, 31.2 mmol) in CH3CN (30 mL) at 0° C. was added DMAP (763 mg, 6.2 mmol) followed by BOC2O (10.22 g, 46.8 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 20 h. The solvents were evaporated under reduced pressure and the residue was purified by flash chromatography (10% ethyl acetate in hexane). The title compound was obtained as a colorless oil which crystallized upon standing (8.33 g, 94%): 1H NMR (400 MHz, CDCl3) δ 1.21-1.32 (2H, m), 1.47-1.48 (18H, 2s), 1.59-1.72 (3H, m), 2.18 (1H, m), 2.85-3.00 (1H, m), 3.89-4.01 (1H, 2d, J 11.9 Hz), 4.47-4.58 (1H, 2br s).

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. customthe residue was purified by flash chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f915e3a54064425c9ea12364bfc5d060
Source dataset
uspto-grants-2008_08
Patent number
US07407964B2

Reaction notes

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