Trimethylsilyl isocyanate → HCID 21930997, compound

HRID 1373430Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N:21]=[C:22]=[O:23])(C)C>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:22]([NH2:21])=[O:23])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

3-(2-tert-Butoxycarbonylaminoethyl)piperidine (500 mg, 2.19 mmoles) was dissolved in anhydrous dichloromethane (10 mL) and trimethylsilylisocyanate (2.96 mL, 21.9 mmoles) was added. The mixture was stirred under argon at 25° C. for 3.35h. The mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic layer was dried (MgSO4), filtered, evaporated to dryness and chromatographed on a silica gel column (15×5 cm) using 5% (10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant to give 3-(2-tert-butoxycarbonylaminoethyl)piperidine-1-carboxamide (417.7 mg, 70%): FABMS: m/z 272.0 (MH+); HRFABMS: m/z 272.1979 (MH+). Calcd. for C13H26O3: m/z 272.1974; δH (CDCl3) 1.16 (1H, m, CH2), 1–30–1.60 (5H, m, CH/CH2), 1.46 (9H, s, —COOC(CH3)3), 1.68 (1H, m, CH2), 1 84 (1H, m, CH2), 2.54 (1H, dd, CH2), 2.73 (1H, m, CH2), 3.08 (1H, m, CH2), 3.42 (1H, m, CH2), 4.02 (1H, m, CH2), 4.10 (1H, m, CH2), 4.84 (1H, m, NH) and 4.96 ppm (2H, bm, CONH2); δC (CDCl3) CH3: 28.5, 28.5, 28.5; CH2: 25.2, 31.7, 34.9, 37.3, 44.6, 50.3; CH: 32.9; C, 79.5, 156.4, 158.2.

Workup

washwashed with saturated aqueous sodium bicarbonate
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
customevaporated to dryness
customchromatographed on a silica gel column (15×5 cm)

Sources & evidence

ORD record: ord-4c66945fb5a648519203b7ac017bd542
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07161003B1

Reaction notes

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