Diethyl Ether → HCID 73853093, compound

HRID 1245593Notes

Reaction equation

HRID 1245593 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(S([N:41]=[N+:42]=[N-])(=O)=O)=CC=1)CCCCCCCCCCC.C(N(CC)CC)C.CCOCC>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])[C:15](=[N+:41]=[N-:42])[C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 109151434-Dodecylbenzenesulfonyl azideHCID 21912749tert-Butyl 4-(3-oxobutanoyl)piperidine-1-carboxylate

Product 1

HCID 73853093HCID 73853093, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.51 g (1.8 mmol) of 1-(tert-butoxycarbonyl)-4-(1,3-dioxo-but-1-yl)piperidine (from Step B) and 0.65 g (1.8 mmol) of para-dodecylbenzenesulfonyl azide (Syn. Comm. 1981, 11, 947–956) in CH3CN at 0° C. was treated with 0.26 mL (1.8 mmol) of triethylamine. The reaction was warmed to rt and stirred for 4.5 hours. The reaction was poured into 100 mL of Et2O and washed with 100 mL of H2O, 100 mL of 2 N HCl and 100 mL of brine. The organic layer was dried over MgSO4 and concentrated. The residue was purified with a 40M Biotage column using 9:1 v/v of hexanes/acetone to afford the title compound as a light yellow oil: RF: 0.33 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.46 (s, 9H), 1.57–1.76 (m, 4H), 2.42 (s, 3H), 2.82 (m, 2H), 3.24 (m, 1H), 4.14 (m, 2H).

Workup

  1. washwashed with 100 mL of H2O, 100 mL of 2 N HCl and 100 mL of brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified with a 40M Biotage column

Sources & evidence

ORD record
ord-986d0c6234aa46b6ad1b6a02ae87cbc8
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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