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

HRID 917515Notes

Reaction equation

[CH:1](I)(C)C.NC1[CH2:11][CH2:10][CH:9]([N:12](C)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])CC1.[CH:21]([N:24]([CH:27]([CH3:29])[CH3:28])CC)([CH3:23])[CH3:22]>C1COCC1>[CH:27]([NH:24][CH:21]1[CH2:22][CH2:11][CH:10]([CH2:9][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:1][CH2:23]1)([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 40 °C

Procedure

Isopropyl iodide (2 equivalents) was added dropwise to a suspension of tert-butyl N-[4-aminocyclohexyl]-methylcarbamate (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-a77279e157b746b49fc2e7057039a1dc
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273880B2

Reaction notes

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