Isopropyl iodide → tert-butyl N-[4-(isopropylamino)cyclohexyl]methylcarbamate

HRID 324522Notes

Reaction equation

[CH:1](I)([CH3:3])[CH3:2].[NH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8][CH2:7]1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH:1]([NH:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:8][CH2:7]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

Isopropyl iodide (2 equivalents) was added dropwise to a suspension of tert-butyl N-[4-aminocyclohexyl]methyl-carbamate (1 equivalent) and diisopropylethyl amine (3 equivalents) in THF. The resulting mixture was stirred for 1 day. TLC analysis showed some starting amine. Additional isopropyl iodide (1 equivalent) and diisopropylethyl amine (3 equivalents) were added to the reaction mixture and heated at 40° C. for 1 day. The reaction mixture was concentrated and chromatrographed to give tert-butyl N-[4-(isopropylamino)cyclohexyl]methylcarbamate: 22% yield, 271 (ESMS, MH+); 1H NMR (CDCl3) δ 4.65 (broad, 1H), 2.91 (m, 3H), 2.42 (m, 1H), 1.80 (ABm, 4H), 1.38 (s, 9H), 0.98 (d, 6H, J=6.3 Hz), 1.32-0.85 (m, 5H).

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-a116b1e9f5c743ed89e91151da5f2266
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218408B1

Reaction notes

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